You already have a sense of what is off.
This names it precisely enough to act on.

When you send the monthly revenue forecast to your team or board, which is closest to what actually happens?

• A I do not have a formal forecast. I track deals in my head and share a rough number when asked.
• B I have a forecast but I adjust the numbers before sharing them. I know the real picture but I present something more confident to keep momentum.
• C The forecast is honest but I am not fully confident in the methodology. Some deals move forward based on criteria, some based on gut. The number is real but I cannot always explain how I got there.
• D The forecast is trusted internally and mostly accurate. Stage definitions exist and the team follows them. I occasionally adjust for context but the underlying data is sound.
• E The forecast runs without me. Stage definitions are documented, followed, and produce consistent accuracy. The team reviews it without my input and I trust what comes out.

When a rep joins your team, how do they learn to sell?

• A They watch me. There is no documented process — I close the deals and they observe.
• B They get some onboarding but mostly learn by doing. The playbook exists in my head. I step in when deals stall because I am the only one who knows what to say at the hard moments.
• C There is a playbook but it is incomplete. Reps can handle early stages independently but they still pull me in when deals get complex. My close rate is significantly higher than the team average.
• D The playbook covers most of the motion. Reps can run deals end to end without me in the room. I get involved in strategic accounts by choice, not necessity.
• E New reps ramp from the playbook alone. My close rate and the team average are within 15% of each other. The motion replicates because it was designed to, not because I am available.

How would you describe your pipeline right now?

• A It is a list of conversations I am tracking. No consistent stages, no shared view with the team.
• B We have a CRM but the data is inconsistent. Some deals are updated, some are not. I do not fully trust the numbers unless I have reviewed them personally.
• C The pipeline is mostly accurate but interpretation varies across the team. We have a single tool but not a single source of truth. I clean it up before reviews.
• D The pipeline is reliable and the team trusts it. Stage definitions are clear. I can forecast from it with reasonable confidence without adjusting.
• E The pipeline is the source of truth for the whole organization. Everyone reads it the same way. Revenue decisions are made from it without my involvement.

How does your company currently approach expansion revenue and renewals?

• A We do not have a formal approach. Expansion happens when a customer asks for more. Renewals happen when the contract date arrives.
• B We track renewals and flag at-risk accounts, but expansion is mostly reactive. CS and sales operate separately and handoffs are inconsistent.
• C We have some structure around renewals and occasional expansion plays, but it is not a designed motion. Good outcomes depend on the individual rep or CSM more than the system.
• D Expansion and retention are tracked alongside new revenue. Handoffs between sales and CS are documented. We have a playbook but execution is still inconsistent at the edges.
• E Expansion and retention compound alongside new revenue. Handoffs are systematic. CS and sales share a single customer view. The motion runs without founder involvement.

If I asked three people on your team to describe your ideal customer, what would happen?

• A I would get three different answers. We have not formally defined who we are selling to — we sell to whoever is interested.
• B I would get roughly similar answers at the high level, but the specifics would vary. We have an ICP documented somewhere but it shifts when a good opportunity outside it appears.
• C The team can describe the ICP consistently. But if I pushed them to name what specifically changes for that customer after they buy, they would struggle. The who is clear. The why is still fuzzy.
• D The team can describe the ICP and articulate the transformation. The thesis is documented. The gap is that not everyone uses it as a filter — we still occasionally pursue customers who do not fit and rationalize it afterward.
• E The team can describe the ideal customer, the problem, the transformation, and the proof — without me in the room. The thesis is the filter we use before pursuing any opportunity. We say no to customers who do not fit.

How consistent is your sales motion across the team?

• A Every rep sells differently. There is no shared process — each person figures it out their own way.
• B There is a loose process but reps adapt it significantly. Some are effective, most are not. The difference between your best rep and your worst is mostly talent, not training.
• C A process exists and most reps follow it. But the close rate drops significantly when I am not involved. Reps can run the early stages but struggle at the moments that matter most.
• D The motion is documented and most reps follow it consistently. Close rates are more even across the team than they used to be. I still close the largest deals but the team handles the rest.
• E The motion replicates reliably. New reps reach consistent performance within 60 days. The difference between top and bottom performers is within a range we can explain and close through coaching, not talent acquisition.

How did you choose the channels you currently use to reach customers?

• A We use whatever has worked so far — mostly my network and inbound that arrived without a clear strategy behind it.
• B We have tried several channels. Some work better than others but we have not made deliberate choices about where to concentrate. We are still running most of them.
• C We know which channels perform best but we have not fully committed to them. We are still spreading effort across too many channels because cutting any feels risky.
• D We have identified our top two or three channels and concentrate most effort there. The strategy is deliberate and data-informed. We are still building the discipline to say no to channel experiments that distract from the core.
• E Channel strategy is validated and concentrated. We know our cost per acquisition by channel and make deliberate trade-offs. New channel experiments are tested against clear criteria before we commit resource.

When the market shifts — competitor moves, changing buyer behavior, new objections — how does your team respond?

• A I notice it first and respond personally. The team does not have visibility into market signals unless I share them.
• B I notice it and eventually update the team. The motion adjusts when I reauthorize the change. Between my interventions the team keeps running the old play.
• C The team surfaces signals but waits for me to interpret them and decide what to change. We adapt but slowly, and always through me.
• D The team surfaces signals and can make incremental adjustments without me. Major pivots still need my input but the team is not waiting for permission to respond to what they observe.
• E The team reads the market and evolves the motion between my interventions. I steward the thesis. The team keeps it current. We adapt faster than our competitors because the capability is distributed, not held by one person.

When a significant operational decision needs to be made — a process change, a resource call, a team structure question — what typically happens?

• A It comes to me. Every significant decision routes back to the founder because the team does not have a framework for deciding without me. My first VP and I are often doing circles on the same decisions, unclear who owns what.
• B Some decisions have been delegated but the boundaries are informal. The team asks me for things I thought I had handed off. I am still involved in decisions that should not need me.
• C Most decisions happen at the right level. But when pressure increases or the situation is new, the default is to escalate. The framework works in steady state. It breaks under load.
• D The decision framework is clear and the team uses it. I am involved in strategic decisions by design, not by default. Escalations happen but they are the exception rather than the pattern.
• E Decisions happen at the closest point to the problem. The team almost never escalates because the operating logic was designed to make the right answer obvious before the question arises. I set direction. The organization decides.

When a new team member joins, what does their first 30 days look like?

• A I onboard them personally. There is no documented process — I explain how things work and they absorb what they can. Each hire gets a different experience depending on how much time I have.
• B There is some onboarding material but it is incomplete. New hires piece together context from multiple people and figure out the rest by asking questions. The experience is inconsistent.
• C Onboarding is documented and mostly consistent. But the documentation reflects how things work now, not how they will work when the team doubles. New hires reach competence but the ramp time is longer than it should be.
• D Onboarding produces consistent results. The process was designed as a unit — new hires get the same context regardless of who is available to deliver it. Ramp time is predictable. The gaps are at the edges where the role requires context the documentation has not yet captured.
• E Onboarding is a scalable unit. New hires reach full productivity on a predictable timeline because the process was designed for volume, not assembled for the current hire. Adding ten people does not require rebuilding the onboarding from scratch.

When your team is under pressure and everything feels urgent, how do you decide what to work on first?

• A We work on whatever is loudest. There is no framework for distinguishing the constraint from the noise around it. The team is busy but progress is hard to see.
• B I set the priorities. The team executes against what I decide is most important. Between my interventions priorities drift because the logic behind my choices has not been shared.
• C Priorities are communicated but the reasoning is not always clear. The team can execute against a list but struggles to sequence independently when new things arrive. They ask me which fire to fight first.
• D The team understands the prioritization logic well enough to sequence most decisions without me. We have identified the constraint and the team knows what moving it first means in practice. I occasionally recalibrate but the framework holds between interventions.
• E The team identifies constraints before they become crises and sequences work against them without waiting to be told. Strategic sequencing is a shared discipline, not a founder skill. The team moves the biggest rock first because the logic for identifying it is embedded in how we operate.

How does your organization maintain alignment across functions week to week?

• A Alignment happens through me. I am in every conversation that matters. When I am not available, things slip or wait.
• B We have recurring meetings but they are inconsistent — often skipped, rarely documented, outcomes rarely followed through. Alignment depends on the right people being in the room, not on the system.
• C The operating rhythm exists and mostly holds. Meetings have structure and outcomes are tracked. But the rhythm was designed for the current team and will need to be rebuilt when the organization grows past its current size.
• D The operating rhythm is deliberate and consistent. Weekly, monthly, and quarterly cadences are clear. The team runs most of them without my facilitation. Alignment is a function of the system, not of my presence.
• E The operating rhythm is a designed unit. It produces alignment at current volume and was built to carry more. The team maintains it without the founder as the forcing function. When something breaks the rhythm, the team identifies it and fixes it.