The War For (Diverse) Teams At Early Stage Companies…and Beyond

Note: Diversity is a term used 30+ times in this piece and refers to all types of diversity, beyond just gender.

In 2004, there was a post-bubble burst resurgence of well funded startups and VMware, like many other companies in the Silicon Valley, was struggling to compete for talent against Google, Yahoo and others in their space. The hot conversation in the weekly e-staff meeting in Palo Alto was about maintaining the bar and hiring the very best talent they could find. This was well before diversity and inclusion was trending as a hiring pain point. There was a war on talent.

To combat this war, the leadership team at VMware got creative. There was an urgency to bring on talent and just competing on compensation and equity wasn’t enough when that talent pool itself was sparse. So, leveraging ties to several of the team members’ east coast roots, they tried an experiment and opened an office in Cambridge, MA.

As the Site Director hired to build out that office at the start of 2005, I was charged with bringing on at least a dozen engineers by the end of the year. I had strict guidance on who to hire first;  the first six hires had to be at least a Staff level engineer, which at that time was like a Principal at most other companies. Even though we were desperate to bring on more talent, the leadership team insisted we still keep the bar high. There were no compromises – hire the best, no matter what.

By the end of 2005, we ended up hiring over 20 seasoned engineers and were well poised to scale that location with more junior talent and expand into other regions across the globe. It was a hard push to win the war, but we won it and many would say that getting scrappy, maintaining the bar and taking risks outside of Palo Alto to hire great talent was one of the key factors that led to VMware becoming the multi-billion dollar success story it is today.

Getting Scrappy And Taking Risks To Create Diverse Teams

Flash forward to 2017, and the talent war is still on, but it’s not just about hiring top talent, it’s about hiring for diversity. There’s plenty of science to prove that diverse teams are what separate average companies from the big success stories. Once there’s diversity in teams, you attract more candidates from underrepresented groups. But there is a catch-22 when companies and teams with no diversity can’t hire candidates from underrepresented groups, in part, because they have no diversity in their current teams!

I was at an event recently where I sat in a breakout session about diversity and inclusion where most of the fifteen or so participants were white, male, CEO-Founders of very early stage companies. These leaders were complaining that despite best efforts, they were not able to find/hire qualified, candidates from underrepresented groups for their open positions. Investors were on their back to meet deadlines and reach revenue goals and the push for building diverse teams was not a high enough priority to push back. They had to hire the best talent they could find, and get coding!

But what if that talent didn’t exist? What if it was 2004 and there were no engineers to hire, never mind engineers from underrepresented groups? How do companies, like VMware did back then, combat this war vs. becoming complacent? What can companies do today to be creative, continue to scale, and develop a diverse team? What if CEOs, their leadership team and their boards held the line on diversity metrics, no matter what?

Starting From The Top

A company that is committed to diversity must demonstrate that commitment from the top, down. CEOs set the tone for the organization’s culture by demonstrating a commitment to diversity and inclusion. They don’t just say they care about the problem and acknowledge the importance of solving it, but they force it to happen. VMware’s founding CEO, Diane Greene, was adamant that we hire only the best talent from day one, and CEOs today need to do the same when it comes to hiring diverse talent.

One of the most compelling reasons for any strong candidate to join a company is knowing there’s diversity at the senior most levels. Having Diane at the helm played a huge role in my decision to join VMware. She was a role model and inspiration to everyone at the company as she balanced the complex demands of scaling our business with her family and other commitments outside of work. We were not only inspired to follow her drive and passion for the business, but the company naturally attracted other strong, candidates because of her leadership.

Whether you are an early stage company, mature business or even just a growing team within a maturing business, committing to diversity at the top is critical. Here are some suggestions on how to do that:

  • The founding team: Diversity does not just have to exist between your co-founding team, it should be among your first hires, your advisors, customers and/or friends of the company. The more diverse the team, the more likely you will be to attract new team members from under represented groups. Introduce prospects to these company “community” members to begin to demonstrate your commitment to this metric at the start. For example, I frequently join interview panels for early stage companies I advise to ensure not just a great hire, but to add diversity to the panel itself.
  • Set and hold the diversity bar for leadership hires: Don’t say “it would be really great to fill the next senior role with a diverse candidate”, rather make it mandatory to create a diverse organization. “We will not hire another manager, director, VP, etc. unless they bring diversity into our team.” Get scrappy and go hard to build these teams (see below). Stop looking for just culture fit and homogenous pattern matching and seek those different than you – they are sure to be additive to your organization beyond just their skills and experiences. Yes, it may take longer to find that person, but hold out for it – it’s worth it!

Note to VCs & Board Members

It is great to see so many VCs and board members stepping up to foster diversity in their portfolios. They are committing to invest in more women founded companies, hosting “diversity events”, making the Decency Pledge and some are creating special funds for diverse entrepreneurs. I believe many VCs are sincerely interested in this effort and not just creating PR tactics to position firms to appear supportive. While those efforts are important to further the cause (don’t stop doing them!), I challenge them to set the bar higher; implementing hard accountability metrics for diversity in their firms and in their portfolio companies. To not be complacent in the reality that it’s “hard to find qualified  candidates from underrepresented groups”, but rather force change to happen. Here are a few suggestions:

  • Mandate that your partnership be a diverse team. Studies continue to come out on how diversity in investment teams have stronger exit outcomes. Get scrappy and find ways to build diverse teams for your firms. The more diverse your team, the more likely your firm, will attract a more diverse group of entrepreneurs into your deal flow. And don’t stop at one – keep forging ahead and strive for a more balanced group of partners; a token diversity hire isn’t enough. Also, each partner from an underrepresented group on your team allows for more diversity on your portfolio companies’ boards. While there’s great debate on whether there’s a direct correlation with diversity on boards and company performance, it is a sure thing that diverse boards add new perspective and new ideas to help the organization succeed.
  • Refuse to fund a non-diverse team (!). Yes, you may have to get your LPs to sign off on this, but many LPs are now pressuring the funds they’re in to push harder on the diversity front. So, take the lead, be proactive and tell them you’re holding the bar. Even if it means an initial slow down on deal flow and longer lead times to exit. The data proves that those investments are far likely to pay off in a bigger way than the non-diverse team investments you’re making today.
  • Set your portfolio teams up for success and help find candidates from underrepresented groups for your investments. Extend runway with a bridge loan or other means until the company has had at least six months to try to shore up their team. Make this a priority of your firm. This too is likely to improve deal flow if you offer this type of support to entrepreneurs as many entrepreneurs are not even coming to you because they don’t have the requisite co-founder, never mind a co-founder/founding team that is diverse.
  • Cover the cost to augment teams during the recruiting process. Not only encourage your portfolio companies to bring in consultants/contractors from underrepresented groups as part of their core team until they demonstrate diversity in their teams, but pay for it! Invest in your teams beyond the equity round.
  • Note to Founders: Depending on urgency to raise capital, you might consider refusing to take money from funds that don’t walk the talk – will your board be diverse? Would non-diverse investment group allow you to fill their board seat with an alternate who brings diversity into the board? The more senior candidates you are courting to join your company will examine board composition carefully – especially if your investors play an active role in the day-to-day of your company (It happens more than we think!). How hard are you willing to work to get a diverse board? Also consider creating a seat for an independent board member from day one to be used if needed to round out your team.

Beyond The Leadership Team And Investors

How are you set up to source for and hire diverse teams? Are you looking in all the right places? In 2015, I wrote a whole primer on hiring for startups (much of which is also applicable for later stage companies), but here are some specific tips on getting creative on hiring for diverse teams:

  • Diversity in your interview panel: Most hiring managers these days know it’s ideal to have a diverse interview panel to help sell a candidate on the role and company, but if your team lacks diversity, consider augmenting the interview team with diverse “community” members – either from other teams in your company or by inviting board members, advisors, friends of the company, etc. to participate. More good info on the hiring process for diversity here.
  • Join, sponsor or network with diversity orgs: There are countless non-profit organizations that cater to diversity hiring causes. For example, joining the National Center for Women in Technology’s Entrepreneurial Alliance which is designed for both startups and incubators/accelerators, provides access to job forums, invitations to their events and connections with over 600 other membership companies. Blackengineer.com has a jobs board, as does lgbtconnect.com. There are loooong lists of other organizations you can tap into to support diversity hiring efforts here, here and here.
  • Bring on Diverse Contractors: To me this is a win-win. You can start getting some work done and having diversity in the office can allay concerns when members of underrepresented groups come in to interview. I’ve heard countless stories of a candidate going for an interview and saying “the whole office was dudes or all white” …you get the visual. I’ve also heard many stories of contractors who fall in love with the company they’re working with (and vice versa) and join full time! (and as noted above, maybe you can get your investors to pay for it!).
  • Never miss the opportunity of a passive candidate: So many companies fail to build diverse teams because they wait for applicants vs. seeking out great people. Troll LinkedIn, go to meetups related to your company’s area, hire sourcers to look for great candidates who may not even know they might want a change until they get a call from your company! Don’t wait for these candidates to come to you.

The First Diverse Hire

Once you reach success and start to hire diverse team members, remember, for many of them, they may be the first one – whether it’s at your company as a whole or perhaps just in one team. There can be an ominous feeling when one thinks they’ve been courted or hired as the token diverse candidate/employee. What will you do to ensure that they are set up for success?

  • Acknowledge the problem from the start. The first time you diversify your team, especially for a small company, the individual will know they are bringing diversity to the table. Speaking from experience, it’s fine to call it out, as long as it’s clear that this is not THE reason they are in consideration. Needing a strong technical leader, or someone who has specific domain expertise is the priority, diversity is simply a value add to the team/company…but don’t dwell on it.
  • Consider how you operate today and whether there are any conscious or unconscious biases towards the current homogeneity of your company/team. Are there activities that happen at work or after hours such as fantasy leagues, spa trips or perhaps even non-family friendly activities that keep the first diverse hire from feeling comfortable or the outlier? Does your office decor offend or intimidate? Carefully examine how your company culture, rituals and environment is setup to be as friendly as possible.
  • You’re not done – the first hire that creates diversity in your team should not check a box and then you move on. Keep at it and for God’s sake please do not make that hire the ambassador for all future diversity activities! It is still the hiring manager/leadership team’s responsibility to keep the momentum.
  • Finally, focus on retaining those great hires.

Make diversity a priority. Hold yourself, your team, your investors and your board accountable. Set standards, get scrappy and change things for the better.

This is a war on for diverse teams. Treat it that way.

Reply in the comments if you have other creative suggestions on how to win the war on creating diverse teams.

So You Want to Be A Product Manager

Because I teach a course on Product Management at Harvard Business School, I am routinely asked “what is the role of a Product Manager?”. The role of a Product Manager (PM) is often referred to as the “CEO of the Product”. I disagree because, as Martin Eriksson points out, “Product managers simply don’t have any direct authority over most of the things needed to make their products successful – from user and data research through design and development to marketing, sales, and support”. PMs are not the CEO of product and their roles vary widely depending on a number of factors. So what should you consider if you’re thinking of pursuing a PM role?

As an aspiring PM, there are three primary considerations when evaluating the role: Core Competencies, Emotional Intelligence (EQ) and Company Fit. The best PMs I have worked with have mastered the core competencies, have a high EQ and work for the right company for them. Beyond shipping new features on a regular cadence and keeping the peace between engineering and the des

ign team, the best PMs create products with strong user adoption that have exponential revenue growth and perhaps even disrupt an industry.

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Do you have what it takes to be the best PM?

Core Competencies
There are core competencies that every PM must have – many of which can start in the classroom – but most are developed with experience and good role models/mentoring. Some examples of these competencies include:

  • Conducting customer interviews and user testing
  • Running design sprints
  • Feature prioritization and roadmap planning
  • The art of resource allocation (it is not a science!)
  • Performing market assessments
  • Translating business-to-technical requirements, and vice versa
  • Pricing and revenue modeling
  • Defining and tracking success metrics

These core competencies are the baseline for any PM and the best PMs hone these skills over years of defining, shipping and iterating on products. These PMs excel at reflecting on where each of these competencies contributed to the success or failure of their products and continuously adjust their approach based on customer feedback.

Emotional Intelligence (EQ)
A good PM may know the Do’s and Don’ts of a customer interview, but the best PM has the ability to empathize with customers in that interview, are tuned into their body language and emotions and can astutely suss out the true pain-points that their product/feature will address. A PM with a high EQ has strong relationships within their organization and they have a keen sense of how to navigate both internal and external hurdles to ship a great product. Here’s a deeper look at how the four EQ key traits, as defined by Daniel Goleman, relate to the PM role:

  • Relationship Management: Probably one of the most important characteristics of a great PM is their relationship management skills. By forming authentic and trustworthy connections with both internal and external stakeholders, the best PMs inspire people and help them reach their full potential. Relationship management is also vital in successful negotiation, resolving conflicts and working with others toward a shared goal which is especially challenging when a PM is tasked with balancing the needs of customers, resource constrained engineering teams and the company’s revenue goals.

    Authentic and trusting relationships within an organization can lead to more support if additional funding is needed for a product or to sway an engineer to include a quick bug fix in the next sprint. Outside an organization, these skills could encourage existing customers to beta test a new feature for early feedback or convince a target customer to try the MVP of a product still in stealth mode. These relationship skills can also be what makes the difference between having irate customers because of a bug introduced into the product and those who say “no worries, we know you’ll fix this!”. 
  • Self-awareness: PMs must be self-aware to remain objective and avoid projecting their own preferences onto users of their products. If a PM is in love with a feature because it addresses their own pain points (PMs are often super users of the products for which they are responsible), they may cause a user to say they love it too just to please the PM (“False positive feature validation”). If not self aware, a PM may push to prioritize a feature they conceived even when all the customer interviews and evidence is stacked against it. This lack of self awareness could derail more important priorities and/or damage the PM’s relationship with engineers who may lose confidence in their PM when the feature isn’t readily adopted by users. 
  • Self-management: Being a PM can be incredibly stressful! The CEO wants one thing, the engineering team another, and customers have their own opinions about feature priorities. Managing tight deadlines, revenue targets, market demands, prioritization conflicts and resource constraints all at once is not for the faint of heart. If a PM cannot maintain their emotions and keep it cool under pressure, they can quickly lose the confidence of all their constituents. The best PMs know how to push hard on the right priorities, with urgency, but without conveying a sense of panic or stress. These PMs also know when to take a breath and step away if needed, regroup, and go back into the game to get sh*t done (GSD). 
  • Social Awareness: According to Goleman, the competencies associated with being socially aware are Empathy, Organizational Awareness, and Service. PMs must understand customers emotions and concerns about their product as much as they understand the concerns of the sales team on how to sell that product (or support team to support it, or engineering to build it). PMs have to have a deep understanding of how the organization operates and build social capital to influence the success of their product – from obtaining budget and staffing to securing a top engineer to work on their product. Finally, social awareness ensures the best PMs service their customers with a product that addresses their jobs to be done which is ultimately what drives product market fit.

Read more about what Paul Jackson has to say about EQ and PMs here – including a sub-link of an interview with Sam Lessin, former VP of Product Management at Facebook, who says he has ‘never successfully trained empathy.’ (or as Lady Gaga would say “you were born this way”…or not!)

Company Fit
So if the best PMs have well developed core competencies and a high EQ, does that mean that they are then destined for success no matter where they work? Going deeper, it is taking these skills and personality traits and applying them to the right company – amid a broad array of opportunities – that will ultimately guarantee success.

I have yet to see a standard job description for a Product Manager because each role is ultimately defined by the size, type of product, stage, industry and even culture of the company. Assuming the core competencies and high EQ as the minimum requirements, the next step is to unpack who’s hiring and what they are truly looking for:

  • Technical Skill – The type of product, who uses it and/or the type of company (e.g. Google who requires PMs pass a technical skills test regardless of what product they’ll work on) will determine how technical a PM needs to be. If the company is building a SaaS CRM, there may be more requirements for experience with go-to-market and customer lifecycles than how the product itself is built. If it’s a data science product with machine learning algorithms and APIs, the role may require a lot more technical depth to not only understand how to build the product but also how to talk, credibly, with the customers who will use it. That said, having a basic technical understanding of what is “under the hood” and mastery of the tools that PMs use is definitely important for the role, anywhere. Colin Lernell has more to say about these necessary skills here.

    If you are an aspiring PM concerned you lack the basic tech skills for the role, you might consider taking online courses such as the renowned Introduction to Computer Science (CS50) course offered by Harvard University or one of the many intro and advanced technology courses offered by The Flatiron School. 
  • Company philosophy about PM – Every company has a different philosophy about the product development process and where PMs fit into that process. Below are the three most common types with pros and cons:

    • PM Drives Engineering: A “throw it over the wall” approach where PMs gather requirements, write the quintessential PRD (Product Requirements Document) and hand it off to Engineering to spec out the technical requirements. Contemporary organizations may do this process in a more agile and collaborative way, but the expectation is that PMs know best about what customers need and engineering is there to serve.
      • Pro: Engineering can focus on coding without a lot of distraction; tends to work well for Waterfall development shops with long lifecycles.
      • Con: Engineers lose sight of the big picture and do not develop empathy for customers which can lead to a poor user experience; often there are unhealthy tensions when tech-debt and “plumbing” work needs to be prioritized against customer requirements. 
    • Engineering Drives Product: More technically oriented product companies (e.g., cloud, big data, networking…) tend to be engineering driven where engineers are advancing the science in their domain and PMs validate solutions or create front end access points (UIs, APIs) to tap into this new technology. There can be a collaborative relationship and feedback loop between customers, PM and engineering, but typically, PMs are serving engineering in these companies.
      • Pro: Breakthrough technology can offer customers things they didn’t even know they needed (VMotion at VMware was a great example of this. An engineer thought it would be cool to do, a PM figured out how to monetize it and it became THE billion dollar game changer for the company).
      • Cons: Engineers chase the shiny new thing, over-architect the solution or iterate forever (seeking perfection) before getting customer feedback; PM input on priorities are ignored, which is sometimes the most basic needs of customers to encourage adoption and increase stickiness of the product.

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    • The PM<>Engineering Partnership: There is a strong yin-yang between PM and Engineering where there is joint discovery, decision-making and shared accountability. Engineers join PMs in customer interviews and PMs are insprint meetings to help unblock tasks or bring clarity to  requirements, but the two roles respect the line where one starts and the other stops. PMs understand what’s being coded, but don’t tell engineers how to code and engineers have empathy for customers’ needs, but leave the prioritization to the PMs.
      • Pros: Streamlined prioritization process that values tech-debt/plumbing projects; better design processes leading to a more positive user experience; higher performing teams with improved product velocity, quality and typically, happier customers.
      • Con: Breakthrough innovation may not get light/investment; time-to-market may seem to lag (but I’d argue what’s released is far better aligned with customer needs with a far more scalable product).

I’m clearly biased (as is Fred Wilson) on the third type of philosophy about PM as I’ve experienced all three and found the yin-yang to be most effective, but it’s not to say the others are notably bad and, again, it really depends on what type of product, stage, etc,. Regardless, when considering a PM role, the philosophy of PM at the company could be the deciding factor on fit for the role.

  • Stage of company – The role of the PM at a startup is far likely to be responsible for “all the things” vs. a mature company where their role will be more distinctly defined. Eriksson, Banfield and Walkingshaw’s book Product Leadership has a section that has a lot more detail on this topic).

    • Startup: Beyond discovery, definition and shipping, they may also be responsible for pricing, marketing, support and potentially even sales of the product. These PMs thrive in a scrappy environment and are comfortable with ambiguity and frequent changes to direction as the company works towards product market fit and learns to operate at scale.
      • Pros: Likely to be more involved with company strategy, exposure to senior leadership/board, able to take more risks/make a bigger impact; more influence/authority over company resources.
      • Cons: Little-to-no mentorship or role models or best practice within the company (may have to seek externally); may not have requisite experience for some of the “things” (comfortable winging it); tight budgets. 
    • Mature Company: The PM may have a more narrow scope (deep vs. broad), have co-workers who handle pricing, go to market strategies, etc.. and likely part of a larger team of Product Managers.
      • Pros: More likely to have mentoring/role models and development standards/best practice; close association with an engineering team can develop strong relationships over time (great for long term impact/career growth); if product has market fit, there is an established customer base and performance baseline to work from vs. guessing until you get it right.
      • Cons: Less exposure to company strategy; just one of many voices of the customer; can get “lost” in the system; more politics; tight budgets. 
  • Founder/CTO/CEO relationship with PM – Especially in earlier stage companies, it’s important to know how involved the Founder/CEO/CTO is in the product process. If they are deeply involved, the PM role may play more of a support role to flesh out their ideas or validate concepts with customers vs. conceiving and driving ideas of their own. This can be great fun for some PMs who enjoy partnering with founders/c-levels and collaborate on the product evolution, but for some PMs it can be very frustrating if they prefer to take more ownership of product direction. It can also be challenging if the more technical founders/c-levels prefer working directly with engineers. This can leave PMs out of the loop or undermined (even if unintentional) causing not just personal frustrations but delays if they have to play catch up and/or continuously recalibrate. When considering a PM role that may work closely with the founding leadership team, be sure to find out their expectations of the PM function and decide whether this is the right fit with your interests.

There are of course many other factors to consider for any role such as the type of product you are building (B2B, B2C, industry, etc.), the humans with whom you’ll work and the overall company culture (diverse, inclusive, flexible work hours, remote culture, etc.), and of course compensation and benefits. There are also a million articles on hiring product managers to get perspective on what the hiring managers are looking for – I especially recommend my friend Ken Norton’s piece How to Hire a Product Manager. However, if you are striving to be the best Product Manager, consider all of the above before signing on to your next gig. Developing core competencies will be an ongoing activity throughout your career and leveraging a high EQ will ensure a more positive experience, but where you work, how they work and who you work with/for will ultimately determine your long term success.

Have additional pointers on succeeding in the PM role? Please share in the comments!

Opening Doors & Taking Action

open doorsAs the news unfolded in the past week over Susan Fowler’s recent blog post about her experiences at Uber, I have been thinking deeply about finding my voice on the matter. I recalled the countless times I had been harassed and never said a thing to anyone, let alone the HR rep at whatever company I was working at the time. I have dozens and dozens of stories of inappropriate, sexually charged, comments from colleagues, winks, suggestive touches, crass jokes, and pictures shared with me that I wish I could unsee. I never called them out.

Fear of gaslighting – being accused of being oversensitive, crazy, blowing things out of proportion – is probably one of the top reasons for not reporting the umpteen incidents employees experience in the workplace. It seems no matter how high we climb the corporate ladder, we still hold back. Whether it’s gaslighting, possible retaliation, or as in Susan Fowler’s case, being totally ignored, we doubt we will be heard.

On those rare occasions when we are heard, those who fall victim to bad behavior or blatant harassment are often “handled” quietly, if at all. Issues are swept under the rug before anyone knows. So, regardless of whether the bad actor gets a warning or more severe action is taken, no one else learns from this lesson. Organizations and leaders desperate to protect their reputations and avoid litigation make it go away a fast as possible. Perhaps those who helped “clean it up” get a reality check, but as long as there is no exposure, no public shaming, no admission of guilt, we will continue to see situations like Ms. Fowler’s persist.

It was a bold move for Ms. Fowler to publicly share her story about Uber and its leadership team’s lack of attention towards her situation. The ubiquity of Uber, and attention the company is already getting in other forums, certainly gave fuel to this issue, but this is not just about tech companies gone bad. It was a rallying cry for leaders at any company, big or small, to not only open the doors for employees to be heard, but to make it clear that crossing the line is no longer tolerated and when it is crossed, action is taken.

Opening Doors
Building a culture of open doors is not just about telling employees “my door is always open,” but actually opening that door. We had a thoughtful series of conversations on this topic at DigitalOcean (DO) over the past week. At our company all hands, we emphasized a zero-tolerance for any harassing behaviors that make our employees feel unsafe and our CEO and I both committed that, while we want people to talk with their managers and our People team first, we are 100% available to talk with any employee who is uncomfortable and prefers to talk with either of us about any issue.

Our commitment to our employees this past week has been well received, but executives making statements about their open doors is only part of the equation. Opening doors is also about ensuring a safe and inclusive work environment by proactively mitigating issues. Ensuring a safe work environment involves everything from setting policies and guidelines to conducting cross-company training beyond the online course we are required to click through when we start a new job.

studentdiscussion_250One of my former employers offered a training using situational role playing to develop understanding and empathy for those who may not appreciate the severity of certain actions. It was an invaluable exercise and we do something similar with the unconscious bias training we provide to all new employees as part of their on-boarding at DO. We’ve found by raising awareness of these behaviors in realistic settings we can do a lot to set clear expectations on what acceptable and unacceptable is, and make people more aware of their impact on others.

If you see something, say something.
Despite proactive efforts, open doors, trainings and policies, harassment still happens. Sometimes, it’s an innocent mistake where a young/inexperienced employee just doesn’t realize they’ve said something wrong. Sometimes, it’s an experienced executive who’s never been called out thus doesn’t appreciate the impact of their behavior. Regardless, we cannot stay silent.

I believe every manager is accountable for reporting any incident that they observe or is reported to them as soon as possible. I also believe it’s every employee’s right to know that their company is taking action to ensure a safe workplace. However, because of corporate policy and privacy protection, we often lack the transparency of how organizations are handling situations and whether they are operating a safe place of work. We cannot, for many reasons, publicly call out every person who crosses a line, but there could be methods(*) to get ahead of this such as:

  • Providing a safe forum for any employee to report an incident they’ve experienced or observed.
  • Tracking anonymized incident data to look for trends including frequency of issues and resolution timeframes.
  • Implementing and broadly communicating Employee Assistance Programs (EAPs) that provide hot lines, advocacy and legal counsel.
  • Internal or even public communication on a company’s performance regarding harassment situations. Imagine a world where companies own unfortunate situations and say how they are resolving them and share improvement data. Scary as that may sound, I bet that if more companies shared this information, the trend of incidents would go down.

The beat goes on…
Whether it was in Twitter or in an intimate setting among friends, Susan Fowler’s story is not the first we’ve heard like this nor will it be the last. We need to continue to bring these topics front and center and commit to continuous improvement in the workplace. I’d love to hear how other leaders are handling this topic at their companies. We all benefit from learning from each other, so please share your stories in the comments.

(*) These are just suggestions, I leave the real policy and program design work to the experts 🙂

The CTO to VP Engineering Fork

bfa_code-fork_simple-black_512x512There comes a time in every scaling tech start-up’s life when an engineering team begins to show signs of needing help. The symptoms can include lost velocity in releasing new products/features, attrition or morale issues, fragile code or lack of innovation. I frequently hear CEOs and founders say “we need a new CTO” or “should we hire a VP of Engineering?”. But what does that really mean? A title is one thing, but the skills necessary to cure the symptoms is a whole other challenge.

Most tech startups have someone serving as CTO — whether it is one of the co-founders or a first senior hire. The role of the CTO is not straightforward and as a company scales, it’s unreasonable for that role to be the end-all-be-all. In the early days of a startup, the CTO is often the chief cook and bottle washer for all things technical. She is coding, serving as the de facto IT person and project manager as well as meeting customers alongside the CEO and helping with hiring decisions. She is expected to be deeply technical and often a domain expert. Firing on all of these cylinders may meet your company’s needs in the short-term, but quite often, there reaches a point where your CTO is no longer being excellent at what they came to your company to do.

In my experience, there tends to be two types of CTOs that evolve as a company grows:

The Evangelist — The shameless promoter of your product, this CTO is out on the road meeting prospects, existing customers and partners and marketing your product. At the same time, they are gathering valuable insight into your product, its pain-points and understanding how it compares to the competition. They are mindful of industry trends and the ecosystem of which your product belongs. They are the ultimate voice of the customer and are keenly aware of the product priorities. They set the vision for the “.next” of your product and the long-term roadmap. They may have once been a coder and understand the basics of your technology architecture. They can go head-to-head with other technology leaders in your space and represent your company at technology conferences. They also tend to be a recruiting magnet for engineering talent.

This CTO works hand-in-hand with the CEO and sales and marketing leads to set the strategy for the company — from market direction to the operations and scale of the business. They are financially savvy and comfortable presenting to and working with your Board of Directors.

The Expert — Often a domain expert or technical guru, this CTO is heads down with your engineering team ensuring your products are built to perform at scale. They may code, sit in code reviews, and mentor junior engineers. They are either designing your underlying architecture or at the very least leading that conversation and signing off on proposed plans. Also talent magnets, they attract senior engineers who wish to learn from this CTO’s experience. They may be key contributors to the open source community, prolific in filing patents, publishing technical papers and speaking at technical and academic conferences. While they enjoy meeting customers and value the insight from those meetings, they prefer more intimate meetings with technical members of customer teams and whiteboard sessions to brainstorm solutions vs. “selling” your products.

This CTO works closely with the sales and support team and often leaves the company strategy and growth discussions to the CEO and other leaders of the organization. They have an opinion on where the company should go, and they’re not afraid to share that, but they leave the details up to “management”.

The VP of Engineering

In both cases above, it’s rare when one of these types of CTOs is also a master at execution. This is when it is important to have a VP of Engineering (VPE). While a VPE can often be someone who can serve as a voice of the customer, be a technical expert and/or represent the company in technical forums, the VPE’s focus is on GSD. Key characteristics of a VP of Engineering are:

  • Process oriented — highly organized around priorities, velocity, quality and meeting deadlines. They have strong project management and communication skills.
  • Great at hiring — pattern matching skills for not just technical expertise, but for people who are collaborative and mission-driven. Knows how to ID the prima donna engineer from the eager-to-learn engineer and when to say “no” even with a great looking resume. Team fit is paramount to success.
  • Great at growing their team — this isn’t about going from 10 to 40 engineers. This is about career development. They’ve got a track record for bringing junior engineers into an organization and developing them into technology leaders and domain experts. Their former engineers have followed them from company to company because they are great to work with. They know how to have fun, but also how to appropriately push a team towards meeting a deadline with urgency and not burn them out.
  • Challenges the status-quo — they won’t just keep building what the co-founders started, but will question both the what and the how. They understand the impact that technical debt can have on the long term scalability of your products. They also know how to tune processes without overkilling the company with process. They are motivated to deliver products and features that customers not only need, but love.
  • Not afraid to get their hands dirty — they lead/attend code reviews, can code if there is an emergency, enjoy tinkering with competitors’ products to understand advantages/challenges of your own products, and appreciate the fine art of squashing bugs. They come in early and stay late when there’s a deadline — even if it’s to make sure engineers are getting food and coffee.
  • Strategic thinker — while a VP of Engineering may not be at the the table deciding the fate of the company, they are part of the discussion. They understand tradeoffs of time-to-market vs. quality and value the need to get a MVP out the door to garner customer feedback early on. They may push for a product or feature, but also respect the larger vision of the roadmap and know when to let go of something that isn’t a priority — in fact, the really good VPE’s kill things sooner than a CTO or CEO may like for the sake of velocity and GSD.

When you’ve decided it’s time to fork that technology leadership role and have both a CTO and a VPE, look for someone eager to create a partnership. Someone who prefers to lean into GSD and growing teams and who values the technology leadership, vision and evangelism of your CTO. Be leery of career CTOs who seek a role as VPE at your company — they may say they’re willing to be in charge of GSD, but could easily step on your CTOs toes. Look for examples of past engineering leadership roles as managers or tech leads. Also look for measurable achievements like improved velocity rates, quality improvements or hiring/team development metrics. Those are telltale signs that you’ve got a solid VPE candidate.

Sometimes it takes a lot of soul searching for a founding CTO to realize they’re not serving the company well around VPE-types of activities. I’ve seen plenty of CTOs worried that with a VPE on board, they’re not sure what’s next for them at the company. I’ve also seen CTOs excel when partnered with a great VPE where they can set the vision and execution strategy in tandem. Fortunately, I am lucky to have such a VPE on board here @DigitalOcean — as well as two awesome Engineering Directors with whom we partner to drive our technology roadmap.

Have you struggled with the CTO to VPE fork? Share your experience in the comments!

Visualizing Mile 26

Boston Marathon

“I don’t know how you do it” seems to be the comment du jour these days. I think it’s a compliment most of the time – an appreciation for everything I have taken on – but I do get this little jab in my brain when I hear it and it makes me wonder if I am insane.

I have a lot on my plate, that’s true. I am the CTO at a growing tech company in NYC, I teach a very hands on course at Harvard Business School in Cambridge. I have three daughters – one college kid in NYC, and a freshman and senior in high school (that’s right folks, college application season, round two!) – and two cats (one of which has a chronic disease requiring daily meds). I manage my household solo (yep, I’m a single mom) and I advise a few companies, coach a few rising stars and sit on a couple boards. Oh, and I occasionally blog.

What?

Ok, so I have taken on a lot, but I simply LOVE everything I do and I make it work by visualizing Mile 26.

I have never run a marathon, but I did the 26 mile Walk for Hunger many years ago with two of my BFFs. I remember being at mile 24 that day and thinking “oh my God, two more miles?!”. I had practically lost my mind because my feet hurt and I was tired and hungry, but instead of throwing in the towel, I just powered on and ran the last 2 miles and left my two friends in the dust, aghast. I had committed to this thing and I wanted to reach mile 26. It was for a good cause and my feet would feel better a week later.

Our lives will always have peaks and valleys. There were many sleepless nights when each of my girls were newborns that I thought would never end. By child three, when I had some experience under my belt, I got through those hard days of barely having time to eat, let alone take a shower, by visualizing Mile 26. The time would come when they’d all be sleeping straight through the night and the days would come when I had to drag them out of bed for school! I was close and I could make it to the end of this phase – Mile 26.

We also have to constantly recalibrate our priorities. When my Dad had major heart surgery back in 2001, I was running Engineering at a tech company and I had two little girls at home. During that time, my mile 24 was several weeks of a daily drive from work to the hospital to home to keep all the balls in the air. I missed many dinners and bath times with the girls, and my work suffered a bit, but Dad was a priority at that time. He eventually was back to himself and under good care at home – Mile 26 – and I was back to having dinner and splashing in the tub with the girls.

I’m not the only one trying to balance so much at once, so here are a few tips and tricks I use to keep it all together (most of the time) that others may find useful:

Give yourself permission to let stuff slide and get help
The school months are my most hectic time of year with many mile 24s (think: 90 degrees and humid running up a hill after 23 miles). I visualize many Mile 26s during this time, like holiday breaks, scheduled trips and the summers when school is out. During these killer mile 24s, I let some stuff slide like that growing pile of clothes I should really get to Goodwill or cleaning out the refrigerator (petrified clementines are cool). I may skip an evening networking event in favor of sleep or to catch up on work and I get help when I need it for errands, home repairs and cleaning (thank you InstacartTaskrabbit and Handy!).

Say “No”, but offer an alternative
As my career has progressed, I get a lot more requests of my time outside of work. I love paying it forward whenever I can, but my cycles are few and I am getting better at saying “no”. I’m flattered by every ask for advice, to speak or to attend an event of some sort. I wish I could do all of it but over the years I’ve learned to become more selective about what I say “yes” to. Whenever I have to say “no”, I try to find an alternative for the requester. Someone else who could coach or speak or attend the event. I find it not only gets me off the hook, but it usually ends up being a great experience for the alternate and very often the requester is quite happy with the result. It’s great when these situations turn into a win-win.

Block time off to GSD
I routinely block off time to make sure I can get stuff done (GSD). Sunday mornings are my most productive times – because #teenagerssleepuntilnoon. I focus on cleaning up my in-box and getting prep work done for the coming week. I have help at work with my calendar, but I do all of the personal stuff myself like making doctor appointments or coordinating carpools. I maximize driving/Uber time for that sort of stuff. It’s important to me that I stay plugged in and not offload everything – especially most things to do with my girls – and there’s something satisfying about getting out of the car and feeling like I just knocked a few things off of my to-do list – mini mile 26s!

[If Applicable] Respect your kids – you only get to do this once
My mile 24 life has taught my girls to be highly independent which is not so bad! They can make themselves meals, do their own laundry and help around the house (ok, with some prodding). That said, I make sure we have dinner at the table together a few nights a week and we have a no cell phone rule at meal time so we can actually talk with each other face-to-face.

I keep an open line of communication for my kids to voice when they need me for anything or feel like my crazy life is not in sync with theirs. When I’ve got a lot going on in a given month, we have “family meetings” where we make sure their priorities for me are in check. For the theater geek, I have a minimum number of shows I must attend (I usually make all of them, tyvm!) and for the sports kid, I have to attend at least two games a season – home or away. I get quality time with my big kid in NYC (perk of the job!) and thank God for texting and social media where we all stay connected probably more than my parents did with me when I was their ages! From Instagram, FB and snapchat to our “My3girlz” text stream that’s endlessly entertaining and annoying 24×7, we are in constant communication.

Take Care of Yourself
If I’m not ok, no one in my life is OK. I do yoga, walk or run a couple times a week. I am a self-proclaimed spa addict and try to get to one at least once a month – even when I was just scraping by early in my career, I made the budget work for this little luxury. I love to travel and take my all three of my girls on a trip together at least one a year. I do acupuncture, sleep eight hours most nights and I am a total freak when it comes to what I put into my body (GF, sorta vegan, organic). I also make time for friends – because friends are what keep me whole beyond my kids. Whether it’s a well needed night out on the town or just a long stream of texts to vent or to laugh, I have an amazing network of people that bless my life.

So, I guess that’s how I do it. I’d be lying if I said it’s a piece of cake. Sometimes I lose it amid a mile 24 and snap at the girls when I’m exhausted and stressed. Sometimes I cancel a few meetings and check out for a couple hours when I’m at work because I need to just think. Sure, a few balls get dropped on the floor – maybe a lot, sometimes – but that’s life and I try not to beat myself up over it. After all, Mile 26 is right around the corner.

Do you take on a lot or wonder how you can take on more? Share your thoughts and concerns in the comments.

Adding Value By Transforming Your Business

business-transformationIn addition to creating a new company that is disrupting the status quo, many founders are also challenging the old norms of how businesses operate in order to add value. When you are struggling to raise capital, hire, and scale your business, is there time and energy available to also rethink how you do business in general? How much effort do you want to put in to stand out as a company not only creating something spectacular, but also a company that differentiates itself as an employer? What truly matters in the end is whether that transformational effort adds value.

In 2012, the gaming company Valve published their novel Employee Handbook  which outlined their organization structure (or lack thereof). Valve challenged the notion of having assigned projects to work on or managers to report to. Many other companies have taken similar approaches not only to attempt to operate more efficiently, but also to attract and retain talent by differentiating their companies from the mainstream.

Whether or not the super flat organization or self-directed projects works, these companies have challenged the standard on how business are “supposed” to run. One could argue that these attempts to be different are distracting and time consuming when the work just needs to get done. However, by taking a chance at doing something different, not only are they attracting new talent, these companies are fueling creativity and innovation across their organizations.

Transforming your business doesn’t always have to be time consuming or distracting. The company Amplitude challenged how businesses handle equity compensation by extending the company options exercise windows to TEN years vs. the standard 90-day window most companies offer. Amplitude also helps employees understand the complexity of their equity plans by outlining in detail the possible scenarios and potential outcomes of their particular grants. The message here is A) you add value to this company and should benefit from it well into the future and B) we want to be sure you fully understand that value as an important member of our team. I imagine neither the window extension or transparency tactics were very time consuming or distracting to implement (well, perhaps the former took some selling to their investors!), but they certainly make this company stand out as an employer and innovator.

Most recently, eShares has stepped up their game by revamping the offer letter. CEO Henry Ward decided that, being in the business of equity management, they should excel in helping job candidates and new employees fully understand what it means to have options in their company. There’s even more to it though, as the offer letter outlines very clearly where a new hire will sit in the organization and what their first week of work will look like. The have transformed the on-boarding process by starting with the offer letter vs. waiting for a new employee to sign and come on board. Perhaps this is an attempt at self fulfilling prophesy (if we tell them about their first week, they’re more likely to accept our offer!), but regardless, the effort to be transparent sets this company apart from so many of the humdrum companies doing the same old thing.

Just because it’s been done that way forever, doesn’t always mean it’s the best way to do business and it certainly won’t set you apart from your competitors. Many entrepreneurs are getting advice from old-school investors and advisors who saw it done a certain way that worked in their day, but that doesn’t mean that’s how it has to be done. If you choose to take a new approach, don’t do it for the sake of being different, do it because it either enables your company to run more efficiently and/or it adds value for your employees or customers.

Have you transformed your business beyond the new products and services you offer to your customers? Share what you’ve done in the comments.

 

Mastering the 1:1

manager one-on-oneWhether you’re a CEO or a line manager, your team is just as important as a group as its members are as individuals. Today’s tech companies offer many perks to attract and retain the best employees. We offer competitive salaries, training and the promise of success – professionally and financially. But how we treat them as individuals can determine the way their DNA will impact the fabric of your organization. What are you doing, as their manager, to make sure they are satisfied and making the best contribution to your organization?

I have managed over 100 direct reports over the course of my career. From the nerdiest, most introverted engineer to the highly extroverted sales executive. They’ve been on either side of up to 20 years senior or junior to me, varying genders and from as far away as India and China to as near as the office next door. No matter what their role, experience, proximity or personality, I have always made their one-on-ones (1:1’s) a priority. Why are 1:1’s so important?

  • Whether it’s an hour a week or 30 minutes once a month, making time for an individual says you give a damn about them as a person.
  • The 1:1 is the only forum where you can have an honest, private, conversation with each other about what’s really going on – professionally and personally.
  • This is a routine opportunity for you, as a manager, to assess the parts (your employees) that lead to the productive whole (your team) – which we all know is more powerful than the sum of said parts.
  • A leader who makes time for their team members – especially those who are also leaders – is less likely to suffer poor team performance because of ambiguity and mistrust. Each 1:1 is an opportunity to clarify the goals of the organization, your performance expectations and build a trusting relationship with your employees by getting to know them as people, not just workers.
  • Finally, constructive 1:1s throughout the year makes performance reviews a breeze. With routine 1:1s, review time can be more about goals and the year ahead instead of constructive feedback from the past.

Don’t just schedule these important meetings with your direct reports, be thoughtful about how these sessions play out. Below is the guidance I give to new managers on conducting 1:1’s.

Set Expectations
Whether your employee has worked for you for awhile and you’re just kicking off 1:1s, or they are a new hire and you’re rolling them into the fold, set expectations up front.

  • I am a big believer in being clear about behavior changes. If this is a new process you are putting in place at your company/in your team, be transparent about it. Otherwise, people worry something bad is going to happen (getting fired) if you all of sudden start scheduling 1:1s. Announce it at a team meeting/all-hands or send out an email/slack being clear about why these are important to do.
  • This meeting is for them as much as it is for you. Be clear that you do this with all employees who work directly for you. No one is being singled out.
  • Book a regular cadence of 1:1s. They should not be ad-hoc. It’s ok to skip one every once and awhile, but having it locked into the calendar is your commitment to being there for your employee.
  • Decide the best cadence with them (weekly or every other week? 30 minutes or an hour?) and what the format should be – your office or theirs, a walk, or maybe grabbing coffee. Different formats work for different employees and they can always be changed as you get into a groove. [see below on remote employees]. Just don’t do after work drinks – that suggests a less serious discussion.

The Agenda
If a meeting is important enough to have, it should have an agenda.

  • Topics in a 1:1 should be about professional growth, personal connection and for giving each other feedback. Do not use the meeting to re-hash things from a group meeting or standup unless there are specific things you took off-line in that meeting or need to provide/get constructive feedback.
  • 24 hours or so before the meeting, email the employee a list of what you’d like to cover. Try to do a split between strategic, tactical and personal items and always ask your employee what they want to cover too. For efficiency, let them know if you need them to bring/read/do something before the meeting. For example:

Jessica, for our 1:1 tomorrow, I’d like to cover the following:
– Review a potential change to the product roadmap for next quarter and how that might impact your team. Please bring the latest roadmap with you.
– Walk through the training presentation deck you are preparing for your new hires. Please send me your latest version tonight if you can?
– Get feedback on whether the budget changes I made for you were helpful. Let me know if there are new numbers I should look at before we meet.
– Hear about your vacation! Your pics looked awesome.

Let me know what else you’d like to cover. Looking forward to catching up!

The 1:1 Meeting
With an agenda set and materials pre-reviewed/in-hand, you are ready for a productive session.

  • Walk through the agenda. Ask if there’s anything else to add before you dig in. Always leave a door open – sometimes an employee is holding back on something.
  • If there are hard things to discuss (maybe some tough performance feedback), try to bookend it with two positive topics. That way, the close of the meeting doesn’t leave your employee feeling down. You’ve given them good feedback and some things to work on.
  • Do not monopolize the conversation. This is for you each to get time to talk. Pause often and make sure there is opportunity for discussion and questions.
  • Always end the meeting asking them how things are going overall and if there is anything else you can do to make them successful. Sounds awkward, but that’s your job! If your employees are a success, you are success.

After the Meeting
It is important to always follow up any 1:1 (or scheduled meeting, for that matter) with notes on what was discussed, decisions made and, if relevant, any constructive feedback that will be measured going forward. Keep it short and sweet:

Jessica, good meeting today! From what we discussed:
– Sounds like the roadmap change won’t slip the schedule much. Please share the new schedule on slack so the team can digest it before our Product group meeting.
– Love the training deck! Let me know if you want to practice with me before you present next week. You’re going to crush it.
– Sounds like those budget tweaks aren’t cutting it for your team’s needs. I’ll try to adjust next quarter, but right now you are going to have to work with what you have. Manage your spend carefully.
– Thanks for letting me know you’re working on a personnel issue on your team. Let me know if I can help. Otherwise, keep me posted on how it plays out.

A recap ensures that you’re both on the same page and it serves as an audit trail if/when anything goes off the rails. Do this with ALL your employees. Otherwise, some may wonder why they’re getting follow up emails and others are not. Consistency in leadership is critical!

Remote Employees and Non-Directs

  • 1:1s with remote employees can be tricky. I recommend using video whenever possible and, if possible, 1-2 in-person 1:1s a year to maintain the personal connection. All other suggestions above apply for the remote employee.
  • It is perfectly OK to have 1:1s with junior people who do not work directly for you. Just remember, you are NOT their manager. Be clear about why you are requesting the meeting.

    Perhaps you are the CEO and want to have a 1:1 with a lead engineer to get a better understanding of a product challenge:

    • Make sure the engineer’s manager knows why you want to have the meeting.
    • Make sure the engineer understands you would like to get the detail directly vs. through other people. You are not going around their boss who knows you are requesting this meeting.
    • Be very careful about feedback. Always end such meetings with next steps being how you’ll follow up with the employee’s manager if there are any action items. Never undermine someone’s manager by giving specific direction without consulting with their manager. Especially if you are the CEO/CTO or other senior position. Often, the most simple “that sounds cool” can be heard as “do it!” from someone more senior than your boss.

Invest in Your Team
One-on-ones can make all the difference in how you lead. Your time invested in doing them right will pay off not only with each individual, but with how your organization functions as a team.

Have other tips on running successful 1:1s or good lessons learned from not having them? Please share in the comments.