When was the last time you got in there with the team and sold a new customer? And not just coming to help close a deal for/with them. But taking your own new prospect all the way through the sales process to a successful close?

The Sales Leader's Dilemma

Yes, sales is like riding a bicycle in that if you haven’t done it in a while you can hop back on, start moving forward, have those early moments of being wobbly and unstable, but then even out and get back into your groove.

You might try to respond like many leaders I deal with do: “Don’t worry, I know how to sell. I sold our _______ enough times to know how it’s done.”

Plus, usually adding an “I am too busy right now to sell.” Or “I don’t want to take leads away from my team.”

In this article, I want to talk about the importance and value of staying fresh and current, selling frequently enough.

The first reason it is so valuable is that people – humans – will generally respect someone as a leader if they feel like that person actually knows how to do the job. If they have done the work they are asking the team to do. Most people will not follow a hypocrite for very long.

In those scenarios where a company hires an external manager/leader, because of their leadership experience and skills, it can be tough for the team to trust and respect them fully if they haven’t sold a mile in their shoes.

The Importance of Leading by Example

If you have been with the team for a while, it is also possible you have new sales team members who haven’t seen you in action. It’s critical that on a regular schedule, you get into the trenches with the team and show them how it’s done!

I always loved those moments where a consulting client’s team that I am coaching and training says to me ‘yeah, but have you ever sold _____?

Do you even know how to sell ____?’

Gauntlet has been thrown…glove has been slapped across my face. Challenge offered. Challenge accepted. At that moment it is now critical that I take up that challenge, pick up a headset – or step forward in the store/booth, and see how good I am.

And every time, after I am done closing the number of sales, or booking the number of appointments that will make it crystal clear that I know what I am doing, I drop the headset, ask if there are any questions, and tell everyone to get back to it.

I have some pretty funny stories about these scenarios, if you ever want to hear them – let me know! (especially the time when the New York, Russian call center CEO thought he knew better than me, but was very wrong)

Building Credibility and Trust

You want to stay fresh, and you want to show your team you are leading from a place of skill and experience, not just management/leadership theory and playbooks.

The second reason, that is more subtle but very valuable, is when the team thinks it’s not possible to succeed. Usually it’s a ‘we can’t close deals/set appointments because of the leads’ moment.

Believe it or not, there are times when a team is blaming the leads or process, and they are absolutely correct.

I have always told my teams that if that moment comes where they think the leads are bad, and the data shows that team wide (not just the underperformers who blame everything but themselves), then I will jump into the queue to experience it myself. It’s not that I don’t trust the team, but I like to be in the conversations myself and get a true gauge – is it the lead quality, sales process, or the team.

When I do that, the team knows that I am willing to investigate, and potentially take their side. In those moments when I do agree with them that it is the leads, it builds a lot of credibility as a leader that I am not just about the ‘company’ and pushing them to succeed, even with crappy leads.

Leading from the Trenches

If sales was a battlefield, your team needs to know that you will pick up a weapon and fight alongside them. That you are as skilled as they are. That you don’t ask them to do things you aren’t willing to do yourself. That you are leading them from a place of understanding and empathy.



How can you build your schedule and routines to allow for those times where you as the coach get to jump into the game and score some points?