How to Be a Working Coach #33: Four Critical Sales Call Strategies

Hi Reader!!

One of the tensions in the coaching world is the relationship between data and outcomes.

Lots of coaches like to point out that what they do is hard to measure. And I believe that's true. But there's another compelling reason to have a data source attached to your coaching: Data can be a revenue stream.

During a recent conversation, I was describing to a potential client why I liked having the Harrison Assessment included in an engagement. My whole motivation was that it makes it easier to develop benchmarks on how a client changes in a coaching conversation.

But when I was preparing the invoice, I realized how valuable it was to the revenue that my practice generates. Having those tools matters…for the client and for the working coach!

Welcome to "How to Be a Working Coach." This is issue number 33. In this edition, we'll examine the three distinct types of sales conversations that every coach must master. Then we'll throw in a bonus sales conversation strategy that might integrate seamlessly into your coaching experience.

Beyond the Single "Sales Call"

Most coaches think about sales as one big conversation - the initial discovery call where everything happens.

But working coaches understand that sales is actually a series of distinct conversation types, each with its own purpose and skills required.

After years of building my practice, I've identified four essential sales conversations that separate working coaches from those who struggle to build sustainable businesses. Master these, and you'll find yourself closing more deals, expanding engagements, and building stronger client relationships.

Full Disclosure: Throughout my coach training, I thought that the moment I launched my website, clients would come. However, the reality is that clients don’t find coaches; coaches find clients.

The hardest hurdle I faced in my coach development was actually learning to run a business and specifically, how to sell. Just like coaching conversations, sales conversations consist of different pieces that form a larger puzzle.

Once you master all four of these, you'll be well on your way to building the working coach practice you've been hoping for.

Conversation Type #1: The Discovery Conversation - Foundation of Everything

Purpose: Mutual Evaluation and Fit Assessment

This isn't just about you discovering if they're a good client - it's about them discovering if you're the right coach. The best discovery conversations feel like consulting sessions where both parties are evaluating whether to move forward.

Key Elements:

• Understanding their challenges using frameworks like SPIN (covered over the last two weeks. Check out past issues here: https://workingcoach.com/profile)
• Assessing coaching readiness and commitment level
• Determining if your expertise aligns with their needs
• Evaluating budget authority and timeline

The Referral Strategy Within Discovery

Here's where many coaches miss a huge opportunity. Not every discovery conversation should end with you trying to close the deal. Sometimes the best business decision is recognizing when you're not the right fit.

I had a recent discovery call where I just kept thinking to myself, "This guy has a personality that needs a very particular kind of coaching. I don't think I would bring the best out of him." I actually said that to him towards the end of the call. He immediately responded, "My gut instinct is that you're right."

OK, confirming.

I passed his contact information on to two other coaches I know, who are very different than me. He's hired one of them. His boss gave me two more names inside the company that he'd like me to do a discovery conversation with, and one is a new client starting in a couple weeks.

It's hard to see how this isn't a win-win-win scenario.

The referral benefits compound:

• The referred client gets what they actually need
• You establish yourself as someone who puts client needs first
• The receiving coach now owes you a professional favor
• Your reputation for integrity spreads through your network

I've tracked this over the years: at least six clients I've referred to other coaches have sent colleagues, friends, or coworkers to me for coaching. As Robert Cialdini explains in "Influence: The Psychology of Persuasion" (Harper Business, 2006), reciprocity is one of the strongest psychological principles in human interaction.

Conversation Type #2: The Upsell Conversation - Expanding Value During Initial Engagement

Timing: During Proposal Development
This occurs after a successful discovery but before a final agreement is reached. You've established they want to work with you - now you're structuring how that work will happen.

Strategic Framework:
Your initial coaching engagement should never be your only revenue stream from a client. The upsell conversation allows you to present additional value that enhances their coaching experience.

Common Upsell Components:

• Leadership assessments (360-degree feedback, leadership style inventories)
• Feedback platforms where they can gather input from stakeholders
• Team coaching sessions to support their individual development
• Strategic planning facilitation to apply their coaching insights organizationally

Every proposal I send features the core offering prominently at the top. However, there are also multiple opportunities to enhance the working relationship with additional add-ons.

The Psychology of Choice Architecture

Instead of presenting a single coaching package, offer three tiers, maybe something like the following:

• Foundation Package: Core coaching engagement
• Comprehensive Package: Coaching plus assessment and feedback tools
• Transformation Package: Full suite including team sessions and organizational components

Often, clients choose the middle option, but the mere presence of higher options increases their perceived value of your services.

Conversation Type #3: The Closing Conversation - Asking for the Business

The most effective closing conversations feel natural, not pushy. After thorough discovery and clear value presentation, the close should feel inevitable.

Example language: "Based on everything we've discussed, I think I could help you, and I sense we'd work well together. What would it take for you to sign our agreement?"
This approach:

• Acknowledges mutual fit assessment
• References relationship chemistry
• Asks an open-ended question rather than pressuring for "yes"

Alternative Closing Strategies:

• The Assumption Close: "When would you like to start our work together?"
• The Choice Close: "Would you prefer to begin with monthly sessions or bi-weekly sessions?"
• The Timeline Close: "To achieve the outcomes you've described, I'd recommend we start within the next few weeks. How does your calendar look?"
  ​

Closing is one of the areas where I have to battle one of my natural tendencies: I don't believe in using 100 words where 10,000 will do (Yes, you read that right. I talk. A lot.). I've learned in the closing conversation to state my case and then quiet down.

Recently, I found a potential client discussing the options out loud, and I simply smiled and nodded while he did so.

After he processed out loud the options, he actually picked the most expensive one with the most upsell options included. I was shocked!

Sometimes, the best closing is no closing at all. Just being engaged with your client and letting them do all the work. Don't oversell after they've already made a decision.

Conversation Type #4: The Renewal Conversation - Building Long-Term Relationships

This conversation actually starts during your current engagement, not at the end of it. The most successful coaches plant seeds for continuation throughout their work with clients.

During the engagement:

• "As we continue this work in future cycles..."
• "This foundation we're building will serve you well as we tackle the next level challenges..."
• "Once we've mastered this skill, the next logical development area would be..."

During a Formal Renewal Process:
Timing: Two sessions before your current engagement ends.
Structure: Request 15 additional minutes at the end of the second-to-last session.

Use a Framework like this:
1. Reflection: "What's been most valuable about our work together?"
2. Progress Assessment: "Where do you see the biggest changes in your leadership?"
3. Future Visioning: "What would you like to tackle next in your development?"
4. Commitment Question: "How would you like our work to continue?"

Part of this is built on the idea that I seek out clients with whom I think I might be able to have a long-term relationship. It's critical to note, though, that I do this by looking for clients who are growing and whose perspective on work and the world might change or evolve over time. Because I actually want to be helpful.
One of the things I do to discover these clients is ask about stories where they've changed in their recent past. And I ask about their areas of growth for what they're focused on in the near future. If they've got something front and center. Very often, this indicates someone who will develop in one area and then set a new target for their subsequent development. That's the client I want to work with.

Multiple Revenue Cycles Strategy

The goal isn't just renewal - it's expansion. Each coaching cycle should naturally lead to deeper, more strategic work:
• Cycle 1: Individual skills and confidence building
• Cycle 2: Team leadership and organizational impact
• Cycle 3: Strategic leadership and succession planning
​

The Conversation I Don't Have: Price Negotiation -- A Personal Confession and Strategy

I'm going to be transparent here: I've learned I'm terrible at verbal price negotiations. Every time I try to discuss cost in real-time, I end up caving to pressure and undervaluing my services.

So I've developed a simple rule: All pricing discussions happen in writing.

My process:

• Discovery calls focus on value and fit, not price
• I send written proposals with clear pricing structure
• I don't negotiate or discuss cost over the phone
• Clients can respond to proposals in writing if they have budget concerns

This approach has several benefits:

• Removes emotional pressure from pricing discussions
• Gives both parties time to consider value versus investment
• Creates documentation of what was agreed upon
• Maintains my pricing integrity and confidence

I've been able to raise my rates by 40% just by handling the price conversation in writing. Someday, I'll get to the point where I don't cave when I talk about it. But that day is not today.

Integration: The Compound Effect of Mastering All Four

Discovery creates trust and positions you as a coach and partner, not a vendor. Upsell maximizes the value of each client relationship from the start. Closing converts interested prospects into committed clients. Renewal builds the long-term relationships that sustain your practice.

Common Integration Mistakes
For Newer Coaches:

• Trying to have all conversations in one meeting
• Skipping upsell opportunities due to fear of appearing "salesy"
• Avoiding direct closing conversations altogether

For Experienced Coaches:

• Rushing through discovery because you "know" what they need
• Forgetting to plant renewal seeds during current engagements
• Becoming too comfortable and not asking for expanded work
  ​

Regardless of where you are in your development, you've got some great opportunities to have this conversation lead to more and more interesting business if you take it seriously.

This Week's Experiment: Two-Part Challenge

Part 1: Revenue Stream Brainstorming (30 minutes) List all potential revenue streams you could offer as upsells:

• What assessments could enhance your coaching?
• What team-based services support individual coaching?
• What strategic facilitation could extend your individual work?
• How could you package these into proposal options?

Part 2: Current Client Analysis (45 minutes) Review your current coaching roster:

• Which clients have three or fewer sessions remaining?
• What would be logical "next level" development areas for each?
• Brainstorm 10 specific ways to frame continuation conversations
• Schedule renewal conversations for any clients ending soon
  ​

Next week in "How to Be a Working Coach", we'll explore "Pricing Like a Pro" - how to structure your fees to reflect your value and avoid the negotiation trap entirely!

What topics would be most helpful for you to dive into? Let us know.

Cheers,

Jonathan Reitz & the Working Coach Labs Team

Brought to You By FLUXIFY If you're thinking about adding an ICF credential or upgrading your credential, or you need a strategy for your renewal, FLUXIFY has you covered. Check out what FLUXIFY Does