Marcy Swenson
Helping founders grow as fast as their companies

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Growth Edge: Waiting Too Long to Hire Leaders Can be Disastrous

Engineering All Hands: San Francisco

There are 8 engineers in the room. Robin Brown, founding CTO, stands up and waves to get everyone’s attention: “Welcome everyone, thanks for coming in; I know you’re all busy building things, and meetings can be a distraction from the real work we love to do.

“I appreciate how hard everyone has worked these past several months; the level of self-organization on this team has been terrific, and the way you have all collaborated to get our initial customers up is mind blowing. As you know, I’ve been out fundraising with our CEO, and we just closed $25M, with Sequoia leading the round, which is a big victory.

“Now we need to work on spending some of that money to improve our product and grow our team. After months of struggling to make payroll, we’ll finally be able to hire a recruiter to help us find more great talent, and manage the recruiting pipeline.

“One of the things I’ve been thinking about is how to grow the team from 8 to somewhere around 30 this year, so that we can ship more features faster. We are such great collaborators that I think the best path forward is to hire more great engineers, and put off hiring leaders as long as we can.

“Speaking of kick-ass teams, everyone on the team has really been knocking it out of the park lately responding to problems, and I know we all really enjoy the adrenaline buzz of averting disaster, which we have done several times over the past few months. I am building a list of security & scalability projects to work on now that we have a bit more breathing room, and we’ll be letting people choose the things that they most want to work on.

“OK, that’s it for now, thanks again everyone, let’s get back to work.”

Robin is at a crossroads and unfortunately not even aware that it exists.Being new to leadership while riding high on the initial success of the small team and recent fundraise creates a common blindspot.

Startup founders go through a typical progression from very early prototype & scrappy team all the way to fully scaled out organizations with professional execs. Founders are called on to grow their teams and their leadership in specific ways at different stages of the organization (or be replaced by others with the skills to do so).

The ability of small teams to self-organize feels so magical and seductive that the leader doesn’t see the cues that things will need to change as the team grows. While it’s hard and time consuming to recruit an engineering leader, the investment pays off when you have someone who can then organize and manage the work and not be consumed doing the work.

While feeling the pressure to grow quickly, Robin has two choices. They can either hire some experienced leaders to work for them, who will help them learn quickly and prevent them from making avoidable mistakes. Or they can keep hiring individual contributors, become overwhelmed by growth and complexity, and then later find that they are unexpectedly reporting to a VP of engineering who has been hired to tame the chaos.

A well-intentioned first time CTO can easily be pulled into the first scenario: they grow their organization by adding ever more individual contributors, but sandbag on hiring experienced leaders. The results are often catastrophic: the CTO works brutally long hours juggling direct reports and projects, the product encounters tragic scalability problems, and eventually a professional VP of Engineering is hired out of desperation by the CEO, because everything is on the brink of disaster.

Robin might choose to postpone hiring leaders, avoid long range planning, and let the team choose how to move forward, because that’s how they want to be led — often the founding CTO has a strong sense of purpose and clear idea of what to do next, and makes the mistake of thinking that the rest of the engineers on her/his team will be equally savvy about what’s needed, and want to be led the same way. As the team grows past the first 10–15 engineers, self-organizing quickly devolves into confusion or infighting between factions, even on the best teams. As the team grows, the CTO is stretched beyond their limit, working ever harder.

CTOs that want to strategically grow have to make the shift from being super reactive, adrenaline based, and solving all the hardest problems themselves, to being thoughtful and targeted about where they expend their energy, and saying no to lots of things they could do well and get kudos for. And it’s not intuitive to do this when you’ve come from a scrappy DIY culture.

Robin and other founders have some or all of these things working against them:

  • Lack of experience hiring (or even working with) senior leaders

  • Deep respect for & easy connections with IC engineering talent

  • Fear that an experienced senior leader will replace them

  • Belief that large teams of engineers will self-organize effectively

  • Suspicion that leadership and management isn’t “real work”

  • Lack of connection with CTO peers that have done this before

  • Desire to look like they have it all figured out & reluctance to ask for help

  • Love of hands-on problem solving that keeps them focused on coding

  • Pressure from CEO to build features & solve customer problems yesterday

  • Existing team members who want to try leadership for the first time

  • Existing team members who balk at bringing in leaders

  • Fear of making an unpopular or wrong move

Given all the pressure to keep building things, the first challenge for Robin in this situation is to realize the urgent need to hire one or more experienced leaders. The second challenge is to focus a significant amount of time on learning how to do so, while postponing other urgent short term wins.

As coaches, there are two things we want to help a CTO figure out: first, when is the right time to start hiring leaders, and second, how will they devote enough attention to get it done when the time is right, and overcome resistance to doing so.

It would be terrific if just reading this (or something like it) convinced Robin to invest in hiring other leaders, but the prevailing forces detailed above are likely to keep them in limbo. Frequently an executive coach or mentor familiar with this challenge is the one to help Robin focus on longer term goals and see the impact of their choices. A skilled coach can help them see and figure out which roadblocks they are running into, and zoom out to the future to understand the consequences of these possible decisions.

Many CTOs we’ve worked with initially see this challenge as “I am too busy to do this right now.” While that is likely very true, a great coach will challenge them to think of the next 6–12 months, and ask “when will you be less busy? How will you know it’s the right time? Imagine yourself 12 months from now — when do you wish you could have started? How would having an experienced leader help you now?” Sometimes there is a critical event (fundraising and thus being able to afford experienced leaders, or a key feature or contract, but often there is just an overwhelming amount of work to be done, and a sense of dread about adding another project to the stack.

If we imagine Robin in this situation, the product has bugs, there have been some scalability problems, the CEO is demanding features, and engineers on the team have pressing architecture questions. Investing in a hiring process that seems hard, slow, confusing and awkward requires continually refocusing on the future, and letting other things fall on the floor. It might feel counterintuitive and wrong, however, it is necessary. It’s often through coaching that the CTO gains enough perspective to stay the course and actually get a new leader all the way through the hiring process.

This is a pattern that repeats frequently for leaders: needing courage and conviction to fail to meet short term demands in order to strategically address a longer term issue. This is Robin’s first time encountering this challenge, which makes it doubly hard. Helping Robin to zoom out and talk about where their team is going to be in 6 months, and then 12 months, how much hiring needs doing, which projects need a capable leader, when they will likely have more time to do hiring, and what the impact of having a skilled leader to support them are all critical thought experiments that will help them figure out the right time to invest in hiring a leader.

Getting Robin to spend regular time thinking strategically about the future shows that there is not a magical time later where they have more time or knowledge about making this hire. This will help them get busy doing the difficult work of figuring out how. It’s *really* hard to see this when you’re in it — the temptation to just build one more feature will always be there. As a CTO gets busier and busier, and zooming out on what’s happening on the team again and again reveals the hopelessness of just hiring more engineers.

There are two ways that we have seen CTOs quickly & effectively grow their teams: the first is hiring experienced leaders to work for them, and them figuring out how to lead people with more experience. The second is hiring a VPE for the entire team, and partnering with them. Leaders who don’t do either one likely have a choice made for them: they will probably end up working for a new VPE, after a number of uncomfortable conversations with their CEO (or one surprise conversation).

If Robin now believes that having additional leadership would be helpful, then we work through the roadblocks and objections to getting started. Probably the most difficult is if Robin doesn’t have a clear idea of what experienced leadership would look like or be able to accomplish. They doubt that anyone could know their situation or their people well enough to replace them. As coaches, we reassure them that these people do exist. They need to learn about what great engineering leadership looks like, by asking other leaders in their network, or even by interviewing and making distinctions between different interviewees. Along the way they will hear stories of terrible engineering leadership, and have to distinguish between the two. If they persevere in either interviewing or talking to other leaders, they gain confidence.

Hiring your first engineering leaders is a go slow to go fast move, and it can be very challenging for a first time CTO. What if the new leaders are smarter & more experienced? It takes maturity and courage to hire people who are more experienced than you, and learn from them, but when you have done this, you have demonstrated your ability to grow.

Written by Marcy Swenson & David Goldsmith