Three Secrets to an Effective Sales One-on-One

One of the favorite things my wife and I like to do together is try out a new brew pub. We live in the Pacific Northwest, and a new microbrewery seems to pop up every week, so there’s no lack of options to explore.

A few weeks ago we were sipping beer (Okay … she was sipping, I was guzzling.), as a couple in the booth next to us sat down and began—what appeared to be—a first date.

It did not go well.

The guy talked and talked and talked and talked, and the poor young lady sat in silence with a forced smile on her face. Sadly, there was not going to be a second date.

It’s my observation that most one-on-one’s between sales managers and their sales reps are a lot like that ill-fated first date. A sales manager talks and talks and talks and talks and a sales rep sits in silence. The difference is, a sales rep can’t decline to go on a second date, but is subjected to bad behavior like this week after week.

This is tragic because the single-most powerful tool in driving sales performance is managers having effective one-on-one’s with their salespeople. They are a proven means for increasing revenue, deepening commitment, and improving productivity.

If there’s one thing you’ve got to get right in sales leadership, it’s having effective one-on-one’s. No exceptions. Here are three secrets for doing just that:

Secret One: Ask Good Questions

Unlike our hapless dating friend, an effective sales one-on-one is making the meeting all about the sales rep and not about the sales manager. The way in which you do that is by asking questions. Honest questions. Genuine questions. Meaningful questions. Good questions.

Good questions ask a salesperson to think for themselves, and not rely on their sales manager to think for them. Good questions allow a salesperson to hear their own voice, building buy-in and creating accountability. Good questions expand organizational capacity and break the bottleneck of dependency most sales managers allow to exist (unintentionally) within their sales team.

The flow of questions in an effective sales one-on-one starts with the past then moves to the present and the future as follows:

Sales One-on-One FlowThe Past: Results

An effective sales one-on-one begins with reality. It does not launch into fanciful dreams for the future without first understanding true business conditions up to this moment in time. Questions about past results are not demeaning or derogatory. They are objective, factual, and posed with the dignity and respect all sales reps deserve.

Here are the questions to ask:

  • What is your sales performance compared to your sales plan for the month?
  • What is your sales performance compared to your sales plan for the year?
  • Where are you in stack ranking with your peers?
  • Where would you like to be? This question applies to all three of the questions above.

Do not under any circumstances give a salesperson the answers to these questions. They will not own the answers if you do. Provide access to the information needed and ask them to share that information with you. The latest, current, accurate information.

After briefly connecting with a rep on a personal basis, this part of your one-on-one kicks-off and frames your meeting with them and shouldn’t take more than five minutes.

The Present: Pipeline Health

Once you’ve framed the sales one-on-one by an honest look at reality, it’s time to explore pipeline health. The present. This will take the bulk of your time with a sales rep and provide the vital information you need to assemble an accurate forecast.

Here are the questions to ask:

  • What new opportunities are in your pipeline today that were not in it the last time we met? What makes each a good opportunity?
  • What existing opportunities have you moved forward in the sales process since we last met? What are the best ways to keep each moving in a positive direction?
  • How does the volume of opportunities in your pipeline support your goals for this month/year? Are any changes needed?
  • How does the distribution of opportunities in your pipeline by stage support your goals for this month/year? Are any changes needed?

The answers you receive to these questions determines how you’ll proceed in your one-on-one. Will you pivot to the right or pivot to the left?

Secret Two: Pivot

The real genius of an effective sales one-on-one takes place here in Secret Two: Pivot. After you ask your questions, listen closely and, based not the answers you receive, adapt your response to the needs of the moment.

Pivot A – Inform and Inspire

If the answers you receive on pipeline health indicate that a sales rep lacks the information he or she needs to move forward successfully, you’re free to talk. Only if, however, you’re convinced the rep really doesn’t know the answers to your questions. If they do know the answers and you jump in and talk, you’re hijacking the one-on-one and preventing learning and accountability from taking place.

If however a rep is truly stuck, give them the information they need and follow that information with the inspiration they also need to do it. In other words, provide direction and then support.

Pivot B – Praise and Polish

If the answers you receive indicate that a sales rep actually has the information he or she needs to move forward successfully, keep drawing them out by continuing to ask good questions (The simple question, “What else?” May be all you need). Limit the talking you do, then, to a bare minimum. Your goal in Pivot B is to help a rep hear their own voice and hold themselves accountable to achieve their own goals. You’re there to facilitate that process, not dominate it.

If you need to say anything, make it polishing—fine tuning—not advice giving. In other words, provide support and then direction (if needed).

The key to doing this well, again, is listening closely and attentively. Don’t think about what you’re going to say next. Ask your questions, shut up, and focus on the response. Then, and only then, open your mouth.

For those of you familiar with Situational Leadership, you’ll recognize the dynamic mix of direction and support in Pivot A and Pivot B. You’ll also noticed that I’ve skipped diagnosis, which on the whole I find to be a theoretical exercise that takes place in a vacuum. Pivoting is much more dynamic, diagnosing on the fly and quickly applying the leadership style needed, live, in the moment. Much more like the real sales world.

Secret Three: Wrap-Up

In wrapping up your sales one-on-one, it’s critically important that you return to asking good questions. This time, however, your questions are about the future, not the past or the present. Or in the words of Paul Simon in his multi-platinum album, Graceland, “Breakdowns come and breakdowns go, so what are you going to do about it? That’s what I’d like to know.”

Here are the questions to ask:

  • What are you going to do in the next week/month to build your pipeline to achieve the results you want?
  • What else? Ask this question repeatedly (and kindly) until all options are exhausted.

Make sure that both of you write down the actions that emerge from the answers to these questions. Capture the commitments made in this part of the meeting and review these commitments at your next one-on-one. You’ll only have to do this a couple of times and your reps will get the idea that you’re a leader who’ll help them become the very best version of themselves, as opposed to a leader who can’t remember from one meeting to the next what they’ve agreed to do.

World Class One-on-One’s, World Class Results

Each part of the sales one-on-one—the past, the present, and the future—teaches your team what’s important in sales. What’s important in sales? Results, pipeline health, and activity.

Don’t deviate from these priorities or delve into hypothetical discussions about sales “strategy.” For that, too, will teach. It will teach that talk’s more important than action (not something you want learned).

Most of us as sales managers are compulsive talkers. We like to hear our own voice and love to give advice. This backfires as badly as a boring first date and alienates those in the meeting with us. Follow this structured plan. Ask the questions I’ve given in each part of the plan, and your one-on-one’s will become world class. So too your results.

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