A commonly seen practice in small and growing companies is to promote the best developer into a leadership role. At first glance, this makes a lot of sense. They’ve proven their capabilities, they know the codebase better than anyone else, and they probably have the respect of the development team. It’s an easy, straightforward, and low risk decision that doesn’t distract from other urgent priorities. In the early days of a startup, it is an expedient choice.
It's important to think ahead though. Your tech leader is a key person whose influence, responsibility, and ability to alter the trajectory of the company grow with the organization, often disproportionally so. Over time, their strengths and limitations will become clearer. Limitations have an opportunity cost or can even cause damage. You need to be confident that the right person is in the role at all times. Confounding the problem, the needs of the role are themselves changing as the organization grows and matures.
So, how do you know if you have the right person?
Technical expertise vs. leadership effectiveness
First, technical expertise and leadership effectiveness are two different skillsets. A skilled developer can run a team of three to four and answer to management while remaining hands-on. In two years, the tech group will be fifteen people spanning four teams with a mix of generalist and specialists. Your sales and marketing teams will have grown as well and will have increased their demands on the developers. And you probably have semi-formalized HR, with formal personnel reviews.
Before you know it, your dev team leader’s role has changed from 80% hands-on, 10% oversight, and 10% reporting to 10% hands on, 60% oversight, and 30% reporting and coordination with other departments.
Can your “best programmer” make the shift? Do they even want to?
If they can’t shift – they’ll spend their time on the fun and comfortable development tasks that they’re used to while the strategic and visionary work that you need gets short shrift.
If they want to shift, how will you help them be prepared for those new responsibilities? Do you have the time to coach and guide them? If not, who will? Is there another executive who can provide mentorship, or should you engage an outside coach? Or would a different person be better suited for the role?
Management credibility, openness, and trust
Tech projects don’t always go smoothly. It’s the nature of the beast – discoveries are made, incompatibilities are found, and sooner or later something needs a workaround.
While these problems are usually not the developers’ fault, it’s up to them to fix them. How does your tech leader respond in these situations? Do they get defensive and make excuses? Do they bring the problem to your attention early or do they clam up until the last minute? Can they describe the problem in layman terms, striking the balance between too much jargon and talking down to the executive team? Can they develop and layout a credible plan for recovery that lets the management team update and respond accordingly?
As the executive team grows, can your tech lead work effectively with the heads of Product, Marketing, Sales, Finance, Customer Success, HR, and so on? These functions all collaborate with and rely on the technical leader, and they usually attract very different personalities. Does your tech lead reach out to and engage these roles, or is software development becoming an isolated silo, mistrusted by other teams?
Technical credibility
The natural trajectory of technical leadership results in being less and less hands-on. But developers want to work for someone who speaks their language, understands their challenges, and can help them work effectively. And technology itself is always changing.
Can your tech leadership strike the balance between the technical and business aspects of their role? Do they stay up to date on the latest developments, or did their tech knowledge become frozen in time at the point when their role flipped to mostly management? Importantly, can they tell the difference between a true technical advancement and one of our industry’s many flavour-of-the-year fads? Can they then construct an impartial justification for initiating, deferring, or rejecting a tech migration based on customer impact and return on investment?
People like to work with those who are like them. A tech leader who stagnates will accrete a development team that is stuck in their ways and cannot adapt to changing business environments. A leader who chases fads will deliver an inconstant architecture with frequent rewrites that delay delivery of new business value. And a tech lead who can’t relate to and engage with their team will deliver a costly rotating door of developers and accompanying knowledge loss.
Wait, you didn’t describe a future risk - you described where I am right now.
Summarizing the above, these red flags are items to consider when evaluating if you have the right person in the role. If you are experiencing one or two of these and your tech leader is open to coaching and reflection, your best path forward is to strengthen them through mentoring.
- High Turnover Rate: If team members are frequently leaving, it could be a sign of poor leadership.
- Communication Breakdowns: Misunderstandings within the tech team or between development and other departments or executives is a strong signal of a problem.
- Reluctance to engage: If other departments implement informal workarounds for interacting with the tech team, or if they have to be prodded to do so, there is almost certainly a leadership problem.
- Missed Deadlines: A leader who struggles to manage the team's workload, fails to prioritize important tasks, cannot balance technical debt and new product development, or consistently misses deadlines is hurting the business.
- Low Morale: If your team seems disengaged or unmotivated, it might be due to ineffective leadership.
- Over-Involvement in Code: If your leader spends more time coding than managing, they may be neglecting their leadership duties.
- Lack of visibility: If the tech team isn’t providing timely updates or is operating as a black box, you have a leadership maturity issue.
If several of these flags are going off, you may have the wrong person in the role. You’re going to need a transition strategy that minimizes risk and disruption. Identify the person you want in the role and plan for how to make the successful transition. Determine if there’s a better suited for the incumbent, and if they’re open to making the transition and aiding their successor.
How NuBinary Can Help
At NuBinary, we understand the unique challenges faced by startups and small enterprises. Our highly experienced Fractional CTO team has experienced and managed these issues for many clients.
Our experts can help you assess whether your current technical leader is the right fit, provide coaching to develop leadership skills, or even step in as an interim leader while leading your search for the perfect candidate.
Our coaching, processes and guidelines can empower your current leader, letting them deliver to the best of their abilities.
Our fractional and interim CTO roster can step in to execute a smooth transition to new leadership, should this be needed.
Our CTO-led recruiting process emphasizes and assess the key skills required of a CTO. Unlike traditional recruiters, we spent years walking the talk ourselves before switching into consulting. We’ve individually worked with hundreds of developers and tech leads, allowing us to make accurate and low-risk assessments of culture, personality, and technical fit.
Contact us at info@nubinary.com for more information or book a meeting to meet with our CTOs here.
