Commercial Growth
Sales coaching for complex deals: how to choose a coach and test the fit
6 mins read
KEY TAKEAWAYS
Coaching for complex deals should work on a real opportunity: the stakeholders, the buyer's evidence, the decision process, the business case and the next executive conversation.
Judge a coach on two things separately: relevant selling experience, and the skill to turn feedback into practice.
Test the fit with one live deal in a sample session, and record the skill worked on, the quality of the feedback, the practical output and the handover.
A study of 1,246 sales reps found managers' coaching skill was linked to goal attainment, while frequent coaching from less skilled coaches was linked to worse results.
Keep the seller's manager involved, so the coaching carries on after the coach has gone.
Good sales coaching for complex deals works on the deals your team is trying to win right now. Choose a coach who has sold in a similar setting and can show how their feedback turns into practice, then test them on one live opportunity before you commit.
The number of sessions and a familiar methodology name tell you little about a coach. Judge them by what changes in the seller's next real meeting, and by whether the seller's manager can keep the work going.
What sales coaching for complex deals should cover
Complex deals involve several people on the buyer's side, a long decision process and a business case that has to survive scrutiny. Coaching should cover each of these, using a real opportunity:
The stakeholders. Who is involved, what each person needs and who can make the decision happen.
The buyer's evidence. What the buyer has said or done that shows the problem is real and the deal is moving. Our guide to sales process stages shows how to tie that evidence to each stage.
The decision process. The steps, approvals and people between today and a signed contract.
The business case. Whether it is built on the buyer's numbers and words, or on the seller's assumptions.
The next executive conversation. What the seller needs to say, ask and agree.
One distinction is worth coaching early. Qualification methods such as MEDDPICC separate a champion from a coach inside the buyer's organisation. MEDDICC describes a champion as someone with power and influence who acts as an internal seller for you and has a vested interest in your success. A buyer-side coach can give helpful insight into the deal but typically lacks the power and influence to be a champion. A seller who mistakes a coach for a champion can believe a deal is stronger than it is.
Coaching builds skill, but it can't guarantee that a paused deal will restart. If the issue is a deal that has stopped moving, check the signs of a stalled deal first.
Check experience and coaching skill separately
A coach needs two things, and having one doesn't guarantee the other.
Relevant experience. Have they sold, or led teams that sold, deals of a similar size, length and complexity? Ask for specific examples.
Coaching skill. Can they watch a seller work, give precise feedback and help them practise until the behaviour changes? A great seller isn't automatically a good coach.
Research points the same way. A study of 1,246 sales representatives in 136 teams at one pharmaceutical company found that managers' coaching skill, measured in a training exercise, was linked to how well their reps met annual sales goals. More frequent coaching was linked to worse results when the manager's coaching skill was low. It covers one company in one industry. For a buyer, it is a reason to check coaching quality, rather than treating the number of sessions as proof of value.
Test the fit on one live opportunity
Ask for a sample session on a real deal before you sign. Bring:
An account map: the people involved and what each one cares about.
The problem in the customer's own words.
The decision steps the buyer has agreed so far.
A draft business case, however rough.
One meeting coming up in the next few weeks.
Then record what you saw. The fields below are a suggested way to compare coaches. They don't describe any one provider's standard session.
Skill under review: the one skill the session worked on.
Feedback quality: how specific the feedback was, and whether it was tied to what the seller actually said or did.
Practical output: a rehearsed conversation, a sharper business case or an agreed action for the next meeting.
Next practice: what the seller will try in a real meeting, and when.
Handover: how the coach proposes to involve the seller's manager.
Use the same record for every coach you test, so you compare like with like.
What executive presentation coaching should change
After coaching, a seller should be able to explain the buyer's problem, the evidence, the options and the decision they are asking for, then handle hard questions. Slide design comes second. Test it in the sample session: ask the seller to present for five minutes, then question them as the buyer's finance director would.
The business case deserves the hardest test. A champion needs material they can use to sell internally, and a polished deck can't replace evidence the seller never gathered. Our article on the B2B buyer journey explains how much of the buying happens before a seller is involved, which is why the case has to stand up without the seller in the room.
Keep the manager involved
Coaching lasts when the seller's manager carries it on. Ask each coach how they hand over to managers: what the manager sees, what they practise with the seller and when the skill is checked again.
Salesforce's coaching advice describes a similar loop: review recorded calls, encourage reps to evaluate their own performance and set improvement goals, and hold them to the commitments they make. Challenger warns against confusing coaching, which develops current skills, with performance evaluation, which presents a picture of the past. A coach who keeps the two apart makes it easier for the seller to be candid about what isn't working.
Judge progress by the behaviour you can see before you judge revenue. A long deal may not close for months, and many things affect whether it does.
Manager, specialist or course?
Use your managers for the weekly rhythm, a specialist for experience your team doesn't have and a course to give everyone the same language. Each has limits.
Your own managers know the deals and the team, and they are there every week. They may lack time, or experience of your largest deals.
An outside specialist coach brings experience of similar deals and a fresh view. They need a clear handover to managers, or the new habits fade when the coaching ends.
A training course gives everyone the same language and skills quickly. It works on general skills more than live deals, so it needs follow-up coaching.
Merlin5's sales enablement page describes first-line managers as the people who set the daily standard and the coaching rhythm, which is why the handover matters.
Where Merlin5 can help
Merlin5's sales execution enablement includes sales coaching, opportunity management, negotiation and executive engagement. Its messaging work covers executive conversation frameworks and presentation coaching. Programmes are designed around each organisation's objectives, and the founding partners have held senior sales and commercial leadership roles.
Where to start
Pick one live deal that matters this quarter.
Write down the stakeholders, the buyer's evidence and the next meeting.
Use it to test a coach in a sample session, with the seller's manager in the room.
Frequently asked questions
Is sales coaching different from sales training?
Yes. Training teaches a skill or method to a group. Coaching helps one person apply it to their own deals, with feedback and practice over time.
Can a top seller coach others well?
Not automatically. Selling and coaching are different skills. Check whether they can explain what they do and help someone else practise it.
How can we judge progress before a long deal closes?
Watch for the behaviours the coaching targets: sharper questions, a business case built on the buyer's own numbers and a clearer decision process in the CRM. Revenue effects can take longer to show and depend on more than coaching.
Sources
Dahling, J. J., Taylor, S. R., Chau, S. L. and Dwight, S. A., "Does Coaching Matter? A Multilevel Model Linking Managerial Coaching Skill and Frequency to Sales Goal Attainment", Personnel Psychology, 69(4), 863 to 894, 2016. https://onlinelibrary.wiley.com/doi/10.1111/peps.12123
MEDDICC, "Sales Champion Definition, Characteristics & Method". https://meddicc.com/what-is-meddpicc/champion
Jen Gustavson, "10 Effective Sales Coaching Tips That Work", Salesforce, 16 June 2022. https://www.salesforce.com/ap/blog/effectively-coach-sales-team-blog/
Challenger, "The Critical Importance of Coaching in Sales". https://challengerinc.com/coaching-in-sales/
NEXT STEP
Practical coaching for complex deals
Merlin5's sales enablement covers sales coaching, opportunity management, executive engagement and presentation coaching, designed around your team's objectives.
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WRITTEN BY
Chris Thomas