Transitioning From Serving to Selling

What to do when things go wrong

It is normal to experience some kind of drag when transitioning from serving to selling. It’s a non-intuitive process in many ways, and a lot of coaches feel like the authenticity of their service fades once they start focusing more on selling. 

The good news is, there are a few main reasons why drag normally happens, and therefore, there are things you can do to lessen its impact on you and your coaching. So in this blog post, I want to show you each of those reasons, explore why they happen, and discuss what you can do about it both in the moment and in the future.

But first, a note about this list of reasons: I created this list from my own practice, from talking to peers, and from working with coaches in the CoachingMBA. It covers most cases that I’ve seen and heard about over the years. But keep in mind that it’s not the be-all and end-all. Drag can be a bit elusive—one kind of reaction by your prospect can have many different causes, and often these causes are layered and hard to tease apart. So if you experience drag in your own practice, you need to stay curious, and keep an open mind to the possible causes—and solutions. 

The other thing to note is that you can do everything right and still experience drag. But if you practice the principles I share in this blog, you will likely experience less drag than most coaches, and be able to smooth out any drag you encounter much more easily. 

So with that said, let’s look at the scenarios. 

1. The Prospect Ambush

What they do: They seem surprised or turned off when you ask them about working together.

Why it happens: Either you didn’t coach them powerfully enough, or (more likely) you didn’t set up the transition into coaching very well. 

Usually, when this happens, it’s because you didn’t tell them you might want to talk to them about the next steps at the beginning of the conversation. As you can imagine, most people don’t like being surprised by an attempt to sell to them, so it’s very important to create the groundwork for a smooth transition early on and avoid surprising them.

What to do about it: If your prospect is indicating surprise by your attempt to transition them, the first step is to slow things down. Own your part in it: you didn’t clarify that this might be a part of the conversation.

Use the moment to check-in with them. Feel into it; see if they want to continue at all. And most importantly, keep serving them. Don’t just push ahead with the selling and let the ball drop on your service, on your value to them, just because you are currently shifting gears. The only thing worse than being surprised by a pitch is being surprised by a pitch that just keeps going. 

2. The Bad First Date

What they do: They hear you invite them to coaching, but they say something about the circumstances that makes them unable to accept in the moment, like about not having the money, or the timing being wrong. Usually, this response has an underlying sense that the experience of your coaching so far hasn’t blown them away. 

Why it happens: This mostly happens when we either don’t serve a prospect powerfully enough, or when they were never really interested in the first place. 

If it’s the latter case, you can’t really do anything about that. But if it’s the first case, how do you know? Well, the only way to really tell the difference is to reflect on how they’ve shown up so far. At the beginning, were they a “HELL YES” to the conversation, or were they humoring you? Did they play along enthusiastically and go full-out, or did they just kind of dabble around?

If they came into the space at first with real enthusiasm, and now they are showing real reluctance, then it’s probably not for a lack of interest. It’s that the conversation wasn’t powerful enough. 

What to do about it: Take coaching off the table completely. Then simply ask: What would you need to know about how we might work together in order for you to be excited about continuing our conversation? 

At this point, what you really want to find out is where you fell short. If possible, you want to keep the door open to you serving them in whatever way works best for them. And to keep serving them despite this. This will also reveal if they were interested in the first place. If they give some vague answer, probably, they were just humoring you when they said yes to the conversation. Maybe they wanted to get some free coaching, or just felt too guilty saying no. This isn’t to say you can’t enroll in this prospect, but sometimes people have agendas. 

So instead of chasing them down, see what you can learn instead. And work on your coaching. I mean, you should always be doing this by practicing and getting feedback, but if this keeps happening, it may mean you need to develop a craftsman mindset when it comes to your work. 

3. The Side Glance 

What they do: The same thing that happens in the Bad First Date, except instead of a feeling of general disinterest, they’re being intentionally vague and shifty. Or they kind of just shut down and quickly get off the call.

Why it happens: They don’t trust you. Maybe, just like in the Bad First Date, they weren’t interested in the first place. But usually, this happens because you failed to create a safe container for them during the initial process. Maybe you coached them without permission, or you failed to go slow enough—either way, they don’t feel fully supported by you and your coaching.

I’ve also seen this happen with coaches who “know exactly what a client needs to hear” and then use a coaching technique known as being annoying, belligerent, and direct. If you think I’m kidding, trust me, I’m not. I’ve seen more than a few coaches do this, and I hate to admit it, but I’ve done it myself. 

What to do about it: When you feel a prospect starting to give purposefully-vague, non-committal responses, the first step is to back away a bit. As you give them space, use the time to assess the situation and determine where their suspicion stems from. 

Here are some possible jumping off points:

1. They’re surprised by your proposal. You didn’t properly set up the transition and they didn’t see it coming. 
2. They’re feeling full. You coached them really powerfully, and they needed space to digest, but you kept going anyway.
3. They don’t trust you. Your container, context, and coaching don’t mesh with their expectations of you. You pushed when you should have invited, or you invited when you should have pushed
4. They don’t understand your value or what your intentions are. You didn’t set-up the context or container well enough to make this clear.
5. They feel alone. You stopped serving them and got in your own head about the future transition, leaving them with an unfinished service.
6. They’re complete. You didn’t assess them properly and you misunderstood their needs at this time.
7. They’re afraid. They don’t believe in themselves, they have a limiting belief, or they have a competing commitment.

Although distrust can stem from a variety of places, the examples above all have one thing in common: the prospect has an assumption about what taking the next step with you will mean, and it makes them hesitant. So if you don’t see this assumption, you start to blame yourself instead. You think it’s about you, and that you’ve done something wrong, so you try to force the connection. But in doing so, you actually push them farther away.

When you know what the underlying issue is, it’s easier to address their concerns and help them feel more confident in the transition to coaching with you.