How to Be a Working Coach #36: Coaching is for Closers! Landing Deals Without the Hard Sell

Hi Reader!!

You sent the proposal three days ago. The discovery call went perfectly. Your potential client seemed excited about working together.

Now you're staring at your inbox, waiting for their response, wondering if you should follow up or if that seems desperate.

Welcome to "How to Be a Working Coach," Issue 36. Most coaches struggle with the window between sending a proposal and getting a signed agreement. Like the song says, "the waiting is the hardest part."

A closing strategy that encapsulates the tension between being professional and being pushy means you can close deals without turning into that aggressive salesperson you promised yourself you'd never become.

It's agony to wait. But how you handle the in-between time matters.

Here's what I mean: once, after a client decided not to work with me, the fact that I was excited about how they had chosen to invest in their future led them to refer all their coworkers to me. So even though I didn't land this engagement, I ended up with 5-6 future coaching engagements, which more than made up for missing out on the original one.

Why Traditional Sales Tactics Fail for Coaches

Executive coaching isn't about selling widgets. You're asking someone to invest thousands of dollars and months of their time in personal transformation. That decision requires trust, not pressure.

When you push too hard, potential clients pull back. They sense desperation. They question your confidence. They wonder if you really believe in your own value. More importantly, aggressive closing tactics contradict everything coaching represents - you're supposed to be the guide who helps executives find their own answers, not the manipulator who pushes them toward saying yes.

One critical component of my sales process is a simple statement, "I think I can help you." But I only say it if I mean it. Leaving a pause after the statement opens the door for the client to make a comment or ask a question. Sometimes I'll add "I'd like the opportunity to see what we could do together."

The simple message is that "I want to help...but only if it works for you."

The Coaching Paradox

Think about your best coaching relationships. They probably started with a genuine connection, not sales pressure. Your clients chose you because they trusted you to support their growth and development. That trust begins in your very first interactions, including how you handle the business side of your relationship.

The Psychology Behind Executive Decision-Making

Executives make decisions differently from other buyers. They evaluate ROI constantly. They've sat through countless sales pitches. They know every closing trick in the book because they've seen their own sales teams use them.

What They're Really Evaluating

Your potential clients are weighing several factors when they look at your proposal:

The Obvious Factors:

• Price and payment terms
• Time commitment and schedule logistics
• Your credentials and track record
• Organizational approval requirements

The Hidden Factors:

• Can I be vulnerable with this person?
• Can coaching create the changes I need?
• What if I fail at this, too?
• How will seeking coaching look to my peers or board?

The Fear Factor

Fear plays a bigger role than most coaches realize. Not fear of spending money, but fear of failure. What if coaching doesn't work? What if they can't change? What if their team finds out they need help? These concerns run deeper than any pricing objection.

Understanding these hidden factors helps you respond appropriately when deals stall. The executive who says, "I need to check my budget," might actually be thinking, "I'm not sure I'm ready to be this vulnerable with someone."

The most common objection I hear is that I ask every client to record every session. I often hear, "Well, my company won't allow that." However, later in the process, clients inform me that they were concerned about having their raw emotional state recorded for posterity. Being prepared to discuss how a recording is part of the package and actually serves the client can help address this point of resistance.

Your Follow-Up Framework That Actually Works

Forget the old "just checking in" emails. You need a follow-up system that adds value while moving the conversation forward. Here's the framework I've developed after years of testing what actually works:

Day 1: The 24-Hour Thank You

After sending your proposal, wait one day and send a brief note:

• Thank them for their time and openness during discovery
• Mention one specific insight from your conversation that stuck with you
• Include one relevant resource (article, podcast, tool) that addresses something you discussed
• Keep it under five sentences

Example: "Thanks for our conversation yesterday about your team's execution challenges. I've been thinking about what you said regarding the disconnect between strategy and implementation. This HBR article on adaptive leadership might be helpful.

Looking forward to hearing your thoughts on the proposal when you've had time to review."

Day 3: The Curiosity Follow-Up

Ask one thoughtful question about their goals. Frame it as genuine curiosity, not sales pressure.

Example: "I've been thinking about what you said regarding your team dynamics. How is that affecting your current quarter's priorities? No rush on the proposal - I'm genuinely curious about this pattern you mentioned."

This shows you're already thinking like their coach, not just waiting for a signature.

Day 7: The Story Share

Share a brief success story from another client (anonymous, of course). Pick a story that mirrors their situation without drawing the parallel explicitly.

Example: "I was just reflecting on work with another executive who faced similar team performance challenges. They discovered that the real issue wasn't the team's capabilities but how decisions were being communicated. This reminded me of our conversation. Happy to explore how this might apply to your situation if you'd like."

Day 10: The Graceful Out

Acknowledge that they might be busy or considering other options. Give them permission to say no.

Example: "I know you're juggling multiple priorities right now. If coaching isn't the right fit for this quarter, I completely understand. Would it help to revisit this conversation in a few months? Either way, I appreciate the thoughtful conversation we had."

This removes pressure and often prompts an honest response about their actual concerns.

Day 14: The Final Value Email

Send the "final value" email, as I call it. Share your best piece of advice related to the specific challenge the potential client faces; something easy to implement immediately, whether they hire you or not.

Example: "Whether or not we work together, here's something you can try this week with your team challenge: [specific actionable advice]. I've seen this create breakthrough conversations in similar situations. Let me know how it goes if you give it a try."

Reading Between the Lines of Client Responses

Silence doesn't mean no. It usually means they're stuck on something specific. Your job is figuring out what that is without interrogating them.

Common Responses and What They Really Mean

"I need to think about it."

• Translation: I'm stuck on something specific, but don't want to say what
• Your response: "That makes complete sense. What specific aspects would be most helpful to think through? I'm happy to provide any additional information that might help."

"It's not the right time."

• Translation: I don't see immediate value, OR I'm in crisis mode
• Your response: Acknowledge their reality. Offer to reconnect at a specific future date. Mark your calendar and actually follow up then.

"I need to check my budget."

• Translation: Maybe budget, maybe value perception, maybe approval process
• Your response: NEVER offer a discount immediately. Instead, explore: "What budget range would work? Would adjusting the engagement structure help? Could you use professional development funds?"

Radio Silence After Initial Interest

• Translation: They're often embarrassed about saying no, or their situation has changed.
• Your response: "I haven't heard back and want to respect your time. I'll assume you've decided to go in a different direction. If anything changes, I'm here."

I remember a client who went completely silent for 3-4 months after an initial proposal was offered. I figured he had changed his mind or decided to do something else. But then we interacted on LinkedIn over an unrelated post. A couple of days later, he said, "Hey, I completely forgot about your proposal because right when it arrived, our company announced an acquisition. It took all of my time. What does your calendar look like if we got started in the next two weeks?"

We started the next Tuesday.

So, don't leap to any conclusions and give your potential client space to say yes on their terms.

The Questions That Close Deals

Good questions do what pressure can't - they help potential clients sell themselves on coaching. Here are the ones that work consistently:

The Cost of Inaction Question

"What happens if nothing changes over the next six months?"

• Let them paint the picture
• Don't rush to fill the silence after they answer
• Listen for the emotional weight, not just the business impact

The Hidden Objection Revealer

"What would need to be true for this to be a clear yes?"

• Reveals obstacles you can actually address
• Maybe they need their boss's support
• Perhaps they want a different meeting schedule
• You can't address concerns you don't know exist

The Readiness Scale

"On a scale of one to ten, how ready are you to start making these changes?"

• Anything below seven means they're not ready
• Follow up: "What would need to shift to move that number up two points?"
• Gives both of you clarity about next steps

The Direct Hesitation Question

"What's your biggest hesitation about moving forward?"

• Direct but not aggressive
• Most executives appreciate straightforward communication
• They'll tell you exactly what's holding them back if you ask clearly

The Future Success Question

"If we were having this conversation a year from now, what would need to have happened for you to feel this investment was worthwhile?"

• Helps them articulate their success criteria
• Also enables you to determine if you can actually deliver what they need
• Creates a shared vision of what success looks like. Vision always has the power to drive a decision.

Creating Urgency Without Being Pushy

Real urgency comes from their goals, not your sales tactics. Connect your coaching to what matters most to them at this moment.

Legitimate Urgency Factors

Timeline-Based Urgency:

• Upcoming performance review
• Major transition or promotion
• Quarterly or annual planning cycles
• Organizational change initiatives

Cost-Based Urgency:

• Calculate what another quarter of their problem really costs
• Quantify the opportunity cost of delayed leadership development
• Frame the investment against the cost of inaction

The Honest Availability Approach

You can mention your own availability honestly: "I typically take on two new clients per quarter and have one spot remaining" is fine if it's true. Making up false scarcity destroys trust immediately.

The Power of Walking Away

Sometimes the most powerful urgency comes from going away: "I want to make sure coaching is right for you at this time. Why don't we put this on hold and reconnect next quarter?" Often, this clarity helps them realize they actually do want to start now.

Your Energy Matters More Than Your Words

Potential clients feel your confidence or desperation through the screen. If you're worried about paying your bills, that anxiety bleeds into every interaction. If you genuinely believe in your value, that certainty comes through just as clearly.

The Pre-Follow-Up Ritual

Before any follow-up conversation, spend five minutes:

• Remember your best client success story
• Feel that pride in the transformation you facilitated
• Remind yourself: You're not trying to convince anyone of anything
• You're offering an opportunity for transformation to someone who might be ready for it

Operating from Abundance

Detachment serves you well here. Yes, you want to help this person. Yes, you'd enjoy the revenue. But you'll be fine either way. This isn't about needing the sale - it's about determining whether you're the right fit for each other at this time.

When you operate from abundance rather than scarcity, everything shifts:

• Your follow-ups feel helpful rather than needy
• Your questions come from genuine curiosity
• Your energy attracts rather than repels

The Graceful No and the Door You Leave Open

Not every prospect becomes a client. How you handle rejection determines whether they might come back later or refer others to you.

When They Choose Another Coach

Celebrate their decision to invest in growth: "That's wonderful that you're moving forward with coaching. I hope it's transformative for you." Mean it. Their success with another coach doesn't diminish your value.

When Timing Isn't Right

Offer to stay connected without sales intent:

• Send occasional value-adds every few months
• Share relevant articles or resources
• Congratulate them on their LinkedIn achievements
• Be the coach who cares about them beyond the transaction

When You Need to Walk Away First

Sometimes you need to bow out gracefully:

• Someone consistently doesn't respond
• They seem unclear about their goals
• They want something you can't deliver

Example: "Based on our conversations, I don't think I'm the right coach for your needs right now. I'd be happy to refer you to colleagues who might be a better fit."

Building Your Confidence Through Practice

Every proposal is practice. Every follow-up teaches you something. Every "no" brings you closer to mastering this process.

Your Learning System

Track What Works:

• Which follow-up emails get responses?
• Which questions unlock honest conversations?
• Which stories resonate with executives in specific industries?
• Build your playbook based on actual results, not theory.

Practice with Peers:

• Role-play with other coaches
• Practice your follow-up calls
• Get comfortable with silence
• Learn to ask powerful questions without attachment to the answer

The more you practice when the stakes are low, the more natural you'll feel when it matters.

This Week's Challenge: Build Your Closing System

Part 1: Lost Deal Analysis (45 minutes) Review your last three lost deals:

• What patterns do you notice?
• Where did communication break down?
• What questions might have unlocked the real concerns?
• What would you do differently now?

Part 2: Follow-Up Template Creation (60 minutes) Create your five-email follow-up sequence:

• Day 1: 24-hour thank you template
• Day 3: Curiosity question template
• Day 7: Story share template
• Day 10: Graceful out template
• Day 14: Final value template

Customize each to your voice. Have your templates ready so you're not creating from scratch each time.

Part 3: Powerful Question Practice (30 minutes) Pick three questions from this newsletter that resonate most:

• Write them in your own words
• Practice saying them out loud
• Imagine different ways prospects might respond
• Prepare your follow-up questions

Part 4: Energy Check Ritual (15 minutes) Create your pre-follow-up ritual:

• Choose one success story you'll remember
• Write down three beliefs about your coaching value
• Practice the feeling of confident detachment
• Test this before your follow-up conversation

Upcoming: Next week in "How to Be a Working Coach", in the last edition of the sales series, we'll explore "The Four Kinds of Offers Every Practice Needs". You'll learn to structure your product listings to give clients a range of opportunities to work with you!

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

Cheers,

Jonathan Reitz & the Working Coach Labs Team

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