Start from what the company needs over the next 18 months, then check each leader against it with evidence: how their team performs, how they hire and what peers say. Develop leaders with peer groups, coaches and operator mentors matched to a specific gap. Share assessments with the founder first, never behind their back.
This is the work most platform people feel least sure about, and it makes sense. You're not on the board. You're not the founder's boss. And you're often asked to weigh in on executives with longer résumés than yours. So a lot of teams either avoid it entirely, or they do it informally, in partner meetings, based on one awkward call with the VP of Sales.
Neither helps the founder. And leadership is often where a company's next year is decided, well before it shows up in the numbers. I spent years as a startup chief of staff, and the hardest moments were rarely about product. They were about whether the team that got us here could get us to the next stage.
The good news: you don't need to be an executive coach to do this well. You need a clear frame, honest evidence and a founder who trusts you.
Assess against the next stage, not the résumé
The most useful question about a leader is whether they can deliver what the company needs next. A great seed-stage head of sales can be the wrong person for a Series B sales org, and that says nothing bad about them.
So start with the company, not the people. Sit down with the founder and write the three to five outcomes the business must hit in the next 18 months. Then go function by function.
| Leader | What the next 18 months require | Evidence so far | Read |
|---|---|---|---|
| Head of Sales | Hire and manage 8 AEs, build a forecast | Hired 2 AEs in 6 months, forecast misses by a wide margin | Gap |
| VP Engineering | Ship the enterprise tier, grow team from 10 to 25 | Hit last two release dates, strong retention on team | On track |
| Head of Finance | Run a Series B process, set up a monthly close | Clean board pack, no fundraising experience yet | Stretch |
| Head of Marketing | Build pipeline for a new segment | New to the segment, founder still owns messaging | Stretch |
Everything in this table is illustrative. The format is what matters: an outcome, the evidence, and a plain read (on track, stretch or gap). "Stretch" is the most common answer, and it's the one where development helps most. For the AI-era version of this scorecard, including how to weigh AI fluency, see how AI is changing the leadership teams startups need.
Gather evidence, not impressions
A leadership read built on one call is just a vibe. Build it from things you can point to:
- Results in their function. Board decks and monthly updates already show whether sales hit plan or releases shipped on time.
- Hiring. How fast do they fill roles, and do good people stay? A leader who can't hire will cap the company.
- Team movement. Senior departures from one leader's team show up on LinkedIn, often before they show up in an update.
- What the founder says, unprompted. If the same name comes up in three updates as "still working on it," that's a signal.
- Peers. Other execs at the company, and sometimes a board member, will tell you how a leader works across the team, if you ask carefully.
Most of this evidence already exists. It's spread across decks, updates, email threads and public profiles. Read it together, company by company, and patterns like repeated senior departures show up well before the founder has to raise them.
Run the conversation with the founder
The founder owns their team. Your job is to help them see it clearly, not to make the call. Do this as a working session, maybe twice a year, framed around the plan rather than around people.
A few questions that work well:
- "If you were hiring for this role today, knowing what you know, would you hire this person?"
- "What do you need from this leader in a year that you don't get today?"
- "Where are you still doing their job yourself?"
- "Who on your team would you hate to lose? Do they know that?"
Write down what the founder says, then share your own read alongside your evidence. If you disagree, say so plainly and kindly. Founders get plenty of polite advice. They need someone who'll tell them the head of sales has missed plan three quarters running.
And keep these notes private to the founder and the platform team unless the founder agrees otherwise. The fastest way to lose a founder's trust is for an assessment to show up in a partner meeting they weren't part of.
Match development to the gap
Once you know where the gaps are, pick a format that fits each one. Generic programs rarely help. Specific ones often do.
| Gap | What tends to help |
|---|---|
| First-time exec, doing the role for the first time | A peer group of leaders in the same role at other portfolio companies |
| Has never run the next stage | An operator mentor who has, for a few months |
| A specific skill, like managing managers | A coach with a clear goal and an end date |
| A founder who can't let go of a function | Partner time, plus a coach for the founder |
| The role has outgrown the person | A search, and a respectful plan for the current leader |
Peer groups are where a platform team can do the most with the least. Put six heads of sales from similar-stage companies in a room once a month (in person if you can). They'll learn more from each other than from any workshop. Your job is the invite list, the room and a good opening question.
Operator mentors come from your network: former executives, LPs who ran the function, alumni of past portfolio companies. If you're building that bench, how to build an expert advisor network founders actually use covers sourcing and matching. When the answer is a search, what portfolio companies need from VC talent teams covers how talent teams support it.
What leadership development actually works for portfolio companies?
Programs tied to a real, current problem work best: peer groups of leaders in the same role, an operator mentor who has done the next stage, and a coach for one specific gap. Generic leadership workshops rarely stick. Start from the gap the founder names, then match the format to it.
Keep each effort time-boxed with a goal you can check. "Over the next three months, the head of sales builds a forecast that lands within an agreed range" is a development goal. "Grow as a leader" isn't.
Check back at the end. Did the gap close? If not, was it the wrong format, or the wrong person in the role? Both answers are useful, and the founder should hear them.
When should a platform team raise a leadership gap with the partner?
Raise it when the gap starts to affect the plan: missed targets in one function, senior people leaving one leader's team, or a founder asking for help with the same person twice. Tell the founder first that you plan to raise it, and bring evidence to the partner, not impressions.
The founder should never be surprised. A short heads-up works:
I'd like to bring the sales hiring gap to the partner this week, mainly so we can line up search support before the board meeting. I'll share what we discussed, the hiring numbers and the plan we agreed. Anything you'd rather I leave out?
Then give the partner something they can act on: the gap, the evidence, what's already been tried and what you recommend. A partner who gets "the head of sales has missed plan three quarters in a row, has hired two of eight planned AEs, and the founder agrees we should start a search" can help. A partner who gets "I'm a bit worried about sales" can't.