Sales Leadership Readiness Self-Assessment

For your top individual contributors weighing the jump into management. Have them take it honestly and alone — this isn't a performance review, it's a mirror.

How to score: Complete all 5 sections. Add for a total out of 120. Interpretation bands are at the end.

Section A — Why do you actually want this? (Motivation Check)

Rate yourself 1 (strongly disagree) to 5 (strongly agree) on each:

1. I want this role because I like helping other people get better at their job, not because it's "the next rung."
2. I've already been informally coaching teammates and found it energizing, not draining.
3. I'm okay with my success being measured by other people's numbers, not my own.
4. I've thought about what I'd give up (my own deals, my own commission ceiling, my own autonomy) and I'm still in.
5. If I never got promoted again after this, becoming a great manager would still be a worthwhile goal on its own.

Section A score: ___ / 25

Section B — Coaching Instinct (Scenario-Based)

For each scenario, pick the answer closest to what you'd actually do — not the "right-sounding" one. Points in brackets, don't read them until after you've answered.

Scenario 1: A rep on your team just lost a deal they were confident about. They ask you what went wrong.

• A) Tell them exactly what you think they did wrong, based on what you saw in the deal. [1 pt]
• B) Tell them it happens to everyone and move on — no need to pile on. [0 pt]
• C) Ask them to walk you through the deal first, and let them find the moment it turned before you weigh in. [4 pt]
• D) Pull the call recording and review it together line by line before forming a view. [3 pt]

Scenario 2: You're two days from the end of the quarter and one rep is $30K short of number, while another rep on your team is stuck on a skill gap that's been costing them deals all quarter.

• A) Spend the two days helping the close-to-number rep find the last $30K. [1 pt]
• B) Split time evenly between both. [2 pt]
• C) Help close the gap where you can add real value in 48 hours, but flag the skill gap as the #1 agenda item for next quarter's development plan — you can't fix a competency gap in 48 hours, so don't pretend to. [4 pt]
• D) Focus on the skill-gap rep since long-term development matters more than one quarter's number. [2 pt]

Scenario 3: A strong rep tells you they disagree with a coaching point you gave them last week and explains why.

• A) Hold your ground — you're the manager, and consistency matters. [1 pt]
• B) Genuinely consider their reasoning, and change your view if they've got a point. [4 pt]
• C) Defer entirely to them since they're closer to the deal. [1 pt]
• D) Table it and move on to avoid conflict. [0 pt]

Scenario 4: You have a rep who is your best performer but is dismissive toward newer teammates and refuses peer-coaching requests.

• A) Leave it alone — their numbers speak for themselves. [0 pt]
• B) Address it directly and specifically, tying it to what you expect from senior reps on the team, even though it's an uncomfortable conversation with your top performer. [4 pt]
• C) Mention it lightly and hope it improves. [1 pt]
• D) Route the newer reps to a different mentor instead. [2 pt]

Scenario 5: In a 1:1, a rep who's missed the number three months running says "I just need better leads."

• A) Agree to push for better lead allocation on their behalf. [1 pt]
• B) Ask them to walk you through their last 5 calls with the leads they did get, before accepting the leads explanation. [4 pt]
• C) Tell them everyone gets the same leads and it's on them. [1 pt]
• D) Suggest they focus more on outbound. [1 pt]

Section B score: ___ / 20

Section C — Letting Go of the Number

Rate 1–5:

1. I can watch a teammate close a deal in a way I wouldn't have chosen, and still call it a win.
2. My sense of accomplishment isn't primarily tied to being the top performer in the room anymore.
3. I'd rather spend an hour helping someone else close a $20K deal than spend that hour closing a $20K deal myself.
4. I'm comfortable with my "output" being invisible for weeks or months at a time (it shows up in the team's numbers, not mine).
5. I don't feel the need to jump in and take over when I see a rep handling a call in a way I disagree with — I'll coach it after, not hijack it during.

Section C score: ___ / 25

Section D — Difficult Conversations

Rate 1–5:

1. I've delivered hard feedback to a peer or friend before and the relationship survived intact.
2. I don't avoid conflict by softening feedback into vague statements ("just keep pushing," "you're doing great").
3. I've told someone something they didn't want to hear about their own performance, in person, not over Slack.
4. I can sit in an uncomfortable silence after asking a hard question instead of filling the space to relieve my own discomfort.
5. I'm prepared to have a compensation, PIP, or termination conversation as part of this role, and I don't think that disqualifies me from also being a good coach.

Section D score: ___ / 25

Section E — Time Horizon & Patience

Rate 1–5:

1. I'm comfortable with success taking a full quarter or two to show up, rather than this week.
2. I can invest real time in a rep's development even if there's a real chance they leave the company or team within a year.
3. I don't need daily proof that my coaching is "working" — I can trust a process I can't always see the output of.
4. I'm willing to spend my first 90 days in the role mostly listening and observing rather than immediately changing things.
5. I've thought about the fact that my own selling skills may atrophy in this role, and I'm at peace with that trade.

Section E score: ___ / 25

Scoring

Add Sections A–E. Max score: 120. (Section B is scenario points out of 20; Sections A, C, D, E are 5 questions × max 5 = 25 each.)

One flag regardless of total score: if Section B (Coaching Instinct) is below 10/20 on its own, don't average it away with a high score elsewhere. Coaching instinct is the one thing this role can't be done well without, and it's the hardest to fake in the first 90 days on the job.