LeadTime#16 - Specialist or Generalist: The Hiring Dilemma
How to choose between deep technical expertise and broader adaptability when hiring? What criteria best serve the team's present and future needs?
Hi, this newsletter is a weekly challenge for engineers thinking about management. I'm Péter Szász, writing about Engineering Leadership and training aspiring and first-time managers on this path.
In this newsletter, I pose a weekly EM challenge and leave it as a puzzle for you to think about before the next issue, where I share my thoughts on it.
Last Week’s Challenge
Last week, we explored a situation where you need to choose between two excellent senior developer candidates - one with deep expertise in your current tech stack who could solve immediate problems, and another with broader experience across different domains but less specific depth. Read the details here if you missed it.
I'll approach this situation with my usual structure:
Goals to Achieve
Execution: Improve our delivery capability by adding the right mix of skills to the team. The new hire should help address current challenges while also contributing to our future direction. Of course, we can never perfectly predict what technology shifts will happen - the future is inherently unknown, so adaptability matters regardless of which candidate we choose.
Team/Organization: Enhance the team's capabilities in areas where we're currently lacking. This works at multiple levels - we should be thinking not just about our team's needs, but also skills the wider organization could benefit from. This is especially true if our team frequently collaborates with others.
Don't just consider your team as it exists today, but as it will likely be in the near future. If the organization is expecting growth, or if some team members are nearing their ceiling and might leave soon, factor that into your decision. Missing context here can lead to a hire that makes sense today but creates problems in six months.
Personal: Create the right balance of challenge and achievement opportunity for the new hire. They should be stretched enough to grow, but not so far that they can't contribute effectively in the short term. Too little challenge leads to boredom; too much leads to anxiety or failure.
Also, consider how this senior hire can help grow others. A great senior developer doesn't just contribute individually but elevates those around them through knowledge sharing, mentoring, and setting technical standards. How will each candidate help develop the rest of your team?
(Tip: I co-hosted a podcast episode with Jeremy Brown discussing What Puts the Senior in Senior Software Engineer? where we discussed in depth how a senior developer contributes to the team beyond technical skills.)
Risks to Avoid
Execution: Over-indexing on either immediate problem-solving or imagined future flexibility. The reality is that our predictions about future technical needs are often wrong - new requirements emerge, technologies evolve faster or slower than expected, and business priorities shift. And just like hiring someone who can't deliver concrete results today, bringing a person on board who’s stuck in a single stack can set them up for eventual failure. In fact, the real risk is hiring someone who works well only in static environments and is not used to learn and adapt.
Team/Organization: Creating unnecessary tension through poor communication about your decision. The team is already divided in their preferences, and without a clear explanation of your criteria, this division could deepen. Be especially sensitive about not appearing to value some team members' opinions over others.
Avoid roles that would isolate the new hire or inadvertently create a "second-class" team. For example, hiring someone to work alone on a new technology while the rest of the team maintains legacy code can be demotivating for everyone involved, creating silos within your team.
Personal: Setting up the new hire for disappointment by selling them on opportunities that may never materialize. If the generalist candidate is excited about working with diverse technologies, but in reality will be confined to your current stack for years, they'll likely become frustrated and leave. Similarly, if the specialist expects to deepen their expertise, but you're planning a tech stack migration, their specialized knowledge might quickly become irrelevant.
5 Questions
What is our validated technical strategy for the next 12-18 months? The emphasis is on "validated" - not just what the engineering team wants to do, but what has buy-in from leadership and product management. Without this alignment, technical aspirations often vanish when business priorities shift. This core question should drive much of your decision - if significant architecture changes are planned and approved, adaptability becomes more valuable. If you're optimizing your current system with no major shifts planned, immediate impact might matter more, and candidates who have experience and future goals in this stack should be preferred.
What skills and perspectives are most needed to complement our team? Look beyond just technical knowledge. Perhaps we need someone who communicates complex concepts clearly to non-technical stakeholders, or who excels at documentation, knowledge sharing, or mentorship. Maybe the team could use someone who can bridge between technical implementation and business objectives. The biggest impact usually comes from adding dimensions the team currently lacks, not reinforcing existing strengths.
How will each candidate grow in the direction we need? A specialist can expand their knowledge breadth over time, while a generalist can deepen specific areas. Based on their learning agility and career trajectory, which candidate shows better capability to evolve with our needs? Past adaptability, not just current knowledge, matters greatly here. Also, consider how their personal goals align with the team's direction - a misalignment will lead to problems regardless of technical match.
What else did we learn from the interviewers? Technical skill assessment is just one dimension. Talk with interviewers individually, especially if you fear that less senior people won't contradict more senior ones in group settings. Sometimes critical information about collaboration style, problem-solving approach, or communication challenges only emerges in one-on-one discussions where people feel safer sharing reservations. Share your concerns about a candidate and see how they agree with you or defend their previous judgments.
What will the onboarding experience look like for each candidate? The first three months often determine long-term success, and coming up with a 30-60-90 onboarding plan can help clarify priorities, which can inform the hiring decision. Who do they need to talk with first? How quickly can each candidate become productive? What support would they need? Who would mentor them? The specialist might contribute faster but in limited areas; the generalist might take longer to learn your specific stack, but could bring immediate value in other ways. Plan the onboarding process for each, and see if that reveals aspects you hadn't considered.
The specialist-versus-generalist dilemma is just one dimension; make sure you don’t get stuck with it only, and consider other aspects too. As usual, concrete, proven work experiences and demonstrable skills should carry more weight than ideas and theoretical knowledge. Past behavior predicts future behavior better than preferences.
Did I miss any important considerations? How would you handle this hiring dilemma? Let me know in the comments!
Next Week’s Challenge
You're managing a team of 9 developers and have been given a modest budget for team building. While delivery is going well, team cohesion needs improvement - newer hires rarely interact with veterans, and people stick to their immediate project groups.
Your team is diverse: different ages, personalities, and working styles. The company has a successful hybrid culture, while most people go to the office at least once a week, two members work fully remote.
You want something meaningful that strengthens relationships beyond the usual happy hours or escape rooms, which tend to have mixed results. The activity should respect different comfort levels while genuinely fostering better working relationships.
What do you do?
Think about what your goals would be and what risks you'd like to avoid in this situation. I'll share my thoughts next week. If you don't want to miss it, sign up here to receive those and similar weekly brain-teasers in the future as soon as they are published:
Until then, here's an inspiring quote related to last week’s challenge:
See you next week,
Péter