In our previous article, we introduced the four types of sales coaching strong leaders use: deal coaching, skills coaching, performance coaching, and career coaching.
Today we’re focusing on the first one: deal coaching.
This is the kind of coaching most sales leaders already do. A salesperson brings you an opportunity, asks for help, and you work through how to win the deal. But there’s an important distinction that separates average leaders from great ones. Helping your salesperson win a deal is not the same as helping them learn how to win deals. Deal coaching done well accomplishes both.
Deal coaching is about helping a salesperson think strategically about an opportunity.
Some deals are simple. Others are far more complex. You might be selling directly to an end user, working through partners, or navigating an organization with multiple stakeholders involved in the decision. Sometimes there are several people influencing the outcome: a business unit leader, a purchasing contact, an executive sponsor, and others behind the scenes. Winning these deals requires more than product knowledge. It requires strategy.
Good deal coaching helps the salesperson step back and think about questions like:
Those answers form the strategy for winning the deal.
Here’s what usually happens. A salesperson walks in and says:
“Hey, I’ve got a deal I want to talk through.”
You ask a couple quick questions. You look at the situation. And then you say something like:
“Good news. Here’s what we need to do. Go talk to this person and position it this way.”
That might help close the deal, but it isn’t coaching. That’s telling.
When leaders jump straight to the answer, the salesperson executes the plan but doesn’t necessarily learn how to think through the situation themselves. And the next time a complex opportunity comes along, they’re back asking for direction again.
Strong deal coaching works differently. Instead of providing the strategy, the leader guides the salesperson to discover it. That means asking questions that push them to think more deeply about the opportunity.
For example:
Who are the decision makers?
Then go a step further.
How do you know they’re the decision makers?
Who do they report to?
Who else might influence the decision?
Where do we stand with each of them?
Some leaders even sketch out a quick org chart with their salesperson to map the relationships. That exercise alone often reveals gaps the salesperson didn’t realize existed. When the salesperson recognizes those gaps themselves, they start developing the instincts strong sellers need.
Another critical part of deal coaching is understanding the customer’s buying criteria. Not just who makes the decision, but how the decision will actually be made. Is the customer focused on price? Convenience? Quality? Risk reduction?
How do you know that? What questions have you asked the customer to confirm it?
Helping salespeople uncover the real decision criteria is one of the most valuable things a leader can do during deal coaching.
One of the hardest parts of deal coaching is resisting the urge to jump in with the answer. Most sales leaders already know what they would do. Giving them the answer feels faster. And it is faster, but it’s not as effective in the long run.
When leaders consistently guide their salespeople through the thinking process, something important starts to happen. Salespeople begin approaching deals more strategically on their own. They start asking better questions earlier and thinking through stakeholder dynamics before problems appear. Over time, they become far more self-sufficient and that frees you up from being in the middle of every deal.
One way to make deal coaching more effective is by using a structured review after important sales calls or meetings. At Pivotal Advisors, we call this a Curbside Check-In Tool.
A curbside check-in allows the salesperson to evaluate how a call went, identify what worked, and determine what could be improved before discussing it with their manager. The leader then reviews the same call and provides coaching based on what they observed. This approach helps identify strengths, uncover gaps, and turn everyday sales calls into learning opportunities for the salesperson.
To learn how to build this tool for your organization, download the guide below.
At its best, deal coaching does more than help close one opportunity. It develops salespeople who can think strategically about complex deals on their own. When your team reaches that point, something powerful happens. You’re no longer required in the middle of every opportunity. Your people can build their own strategy, which frees you up to focus on the bigger leadership priorities.
That’s the real goal.
© Pivotal Advisors, LLC | Privacy Policy
