Six months into 2026, the signals are clear: your leadership team is either aligned to this year’s strategic priorities, or they aren’t.
That does not always mean someone failed. The leader who was right in January may not be the leader your company needs in June. Markets shift. Customer signals sharpen. Revenue pressure builds. The goalposts move. We hire for specific capabilities, and even great leaders cannot fit every mold.
But if your priorities were set clearly from the start, and still matter now, midyear gives you real evidence. You can see who turns strategy into execution, and who owns the hard calls. Who adapts without constant direction. Who needs too much from you to keep momentum moving.
For Seed and Series A founders, midyear is the moment to step out of the weeds and look closely at the team carrying the company forward. It is a time to take stock of who you have, what the business now needs, and whether your leaders are still aligned to the road ahead.
Because when context changes, the leadership mandate changes with it. The executive who was right six months ago may still be right today, but alignment cannot be assumed. It has to be reassessed.
Brian Halligan, HubSpot’s co-founder, estimates that roughly 40% of executive hires don’t stick 18 months after they’re made. At the founding stage, the window can be even shorter.
The Case for a Midyear Leadership Checkpoint
Founders do not have the luxury of waiting six months to address obvious leadership gaps. If someone is actively failing in their lane, every week matters.
But not every concern is a failure pattern. Some signals are noise, some are coaching moments, and some are early warnings of a deeper mismatch. That is why leadership assessment needs discipline, not constant vigilance. Daily suspicion drains energy and distorts judgment. Ignoring persistent issues is just as costly.
Midyear creates a chance to memorialize your leadership assessment, and a moment to separate what needs immediate correction from what needs a bigger leadership decision. By June, you have seen how your leaders handle pressure, shifting priorities, hard tradeoffs, and the gap between the role they were hired for and the role they are actually doing.
Use that evidence. Look at each leader against today’s priorities, not yesterday’s assumptions. Ask where they create leverage, where they still require too much from you, and whether they can carry the next stage without constant direction.
The Midyear Leadership Read
By June, four leadership signals are usually visible.
1. Who became more useful when the plan changed?
Every early-stage company changes its plan to some degree. The question is who became sharper as the picture shifted. Look for the leaders who moved through ambiguity, clarified tradeoffs, and helped the company make better decisions. Then look at who needed you to translate every change into direction.
2. Who is the organization routing around?
Workarounds are leadership data. When people quietly compensate for one executive, follow the signal upstream. That can look like softening their communication, re-explaining decisions, managing around gaps, or going elsewhere for answers. It might be communication, structure, or fit.
3. Where is confusion showing up below the leadership table?
Executive misalignment rarely stays contained. It shows up two layers down as duplicated work, unclear priorities, delayed decisions, or teams that are busy but not moving in the same direction. When the org feels foggy, trace the fog back to ownership, decision rights, and executive alignment.
4. Who is creating leverage, and who is creating dependency?
By midyear, you can usually see which leaders are scaling with the business. The strongest executives expand the company’s capacity without making themselves the center of every solution. Be careful not to confuse rescue behavior with leadership. You are looking for leverage, not heroics.
Before You Decide What the Signal Means
Turn the lens inward before you turn it outward.
Did your leaders have clear priorities, or were they expected to infer them? Did the mandate change without being named? Did you tolerate workarounds because someone was loyal, early, or once essential? Did you reward rescue behavior because it kept the business moving, even if it created dependency?
Founder accountability does not mean absorbing every leadership gap as your fault. It means being honest about the conditions you created before deciding what the signal means.
Sometimes the gap is the leader. Sometimes it is the role. Sometimes it is the structure. And sometimes, the founder has not made the next chapter clear enough for anyone to lead it well.
When the Read Surfaces a Gap
Not every gap needs the same response.
A coaching gap means the leader has the right instincts, but needs clearer expectations, more direct feedback, or different operating conditions.
A role-fit gap means the business has outgrown what the hire was built for. The person may still be talented, trusted, and hardworking, but the role has become materially different from the one they stepped into.
A structural gap means the issue is not the person. It is where the function sits, what it owns, how decisions flow, or what the company is asking one role to carry.
A judgment gap is different. This is when the leader repeatedly makes calls that erode trust, slow the business, or require the founder to stay too close. This is the hardest one to coach, and the most important one not to rationalize.
The mistake is treating every gap like a performance problem. Strong founders diagnose the type of gap before deciding the next move.
Before you open a search, get clear on whether you are replacing a person, redesigning a role, or upgrading the mandate. Those are three different decisions.
A Closer Look at the Engineering Leader
At Seed and Series A, few hires matter more than your first Engineering leader. And if you are not a technical founder, evaluating that hire requires outside perspective and a focused six-month post-mortem.
Melanie Dabu, who leads DK Recruiting’s executive and technical search division, advises founders to use the six-month mark to revisit some of the questions that should have guided the hire from the start:
- What was most broken, fragile, or exposed before this leader joined — and is it stronger now because they are here?
- What milestone did we hire them to reach, and are we on track?
- What problems did we assume they had already solved before joining, and do the problems we are facing now match that experience?
If your answers hold up, you likely have the right builder. If they don’t, you now have a specific diagnosis instead of a vague sense that something is off, which is exactly what makes the next decision easier.
Mel also flags three places founders quietly get this read wrong. One is your own leadership style. Be honest about whether you hired this person to challenge you or to agree with you, and how that dynamic is working in action. Another is the board. Notice how much of the original hire reflected a board member’s preference, and whether that weight still holds up against two quarters of real data. Were you and the board aligned in what this Engineering leader would be brought on to do, and why? The last is the one most founders skip, and it comes straight from engineering practice: ask the people doing the work. Engineers who are hands-on-keyboard every day can surface insights that productivity metrics alone will never capture. Instrument the system and talk to the people closest to it.
The Bottom Line
The best founding teams are not accidents. They are built by founders who stay honest about what the signals are telling them, including the signals they may have helped create.
June is a good window to do that with discipline.
If you are starting to see a leadership gap and need a sharper read on whether it is coaching, role-fit, structural, or time to think about the market, DK Recruiting can help you pressure-test the signal before you make the next move.
Use the calendar link below to book a pro-bono, 30 minute leadership assessment with Managing Partner Cassie Rosengren: https://calendar.app.google/oGyxDU5hgJh4jTTP8
