The Problem

We continue our quest to ask for budget for coaching (or anything else) like a strategic leader. 

Let’s recap. 

You’ve had your initial conversation with your manager. You’ve aligned on goals. You’ve explored existing resources. You’ve agreed to develop a plan.

And now? You think it’s time to get coaching referrals, speak with a few coaches, find your match and go back to your manager with, "I found this great coach who can help me get where we want to go."

Not. Quite. Yet.

The Discovery

Imagine this:

After you spend all that time researching and speaking to coaching, you confidently say, "I found this amazing coach I’m excited about working with who focuses exactly on the goals we discussed." Your manager, not missing a beat, fires back:

"What about a mentor? I had one who changed my life."

Congratulations, you’ve run into an objection.

In sales, an objection is a doubt or concern that prevents someone from moving forward to approve a purchase. People typically respond to objections in one of two ways:

“Oh, okay... I guess I could do that.” (You fold because you don’t know how to respond.)

“But I think an external coach would be better for XYZ.” (You start defending, which causes your manager to double down, and the conversation goes in circles.)

One way to get ahead of this sticky spot? Evaluation criteria.

Evaluation criteria are the benchmarks your manager uses to assess the effectiveness of your proposal. Even if you’re aligned on the goals, how you achieve them might not be as clear.

Believe me, your manager has a vision for what your plan should look like, even if they haven’t vocalized it yet. And if you don’t take the time to align on evaluation criteria, you’ll spend hours developing your plan only to find out it doesn’t meet their expectations.

The Experiment

1. Define Your Evaluation Criteria

Last month I talked about presenting your leadership goals with a clear point of view instead of leaving all the work to your manager. Same applies here. Before you even bring up coaching, consider how to design your leadership development plan in the way you really want. Here are a few options to think about:

These aren’t as binary as a table makes them out to be. A mentor can provide coaching. A coach can share advice. There can be hybrids for most of these categories. The key is understanding the tradeoffs.

Reflect on these options and decide what you really want. Does coaching still seem like the right fit for you right now? Maybe, maybe not. 

2. Remember Who’s Leading

Let’s say you’ve decided that 1:1 coaching with an external coach, meeting monthly, is the best fit. Now it’s time to align with your manager on the evaluation criteria. You’ve likely done more thinking about this than your manager has. So, take the lead on the conversation.

Start by reminding them of the goals you’ve already aligned on:

“I’ve been reflecting on our last conversation and the goals—ABC—and how to achieve them most effectively. I’ve considered a few options, like 1:1 coaching, group coaching, live sessions, and mentorship. Can I get your input on my proposed approach?”

Now’s your chance to share your thinking and walk them through it. Be clear, be concise, and don’t be afraid to ask for their feedback.

3. Handle Objections

When you encounter resistance, that’s not a bad thing. It’s actually an opportunity to dig deeper. If your manager mentions their life-changing experience with mentorship, don’t reflexively accept or defend. Summon your curiosity and dig deeper.

• It sounds like your mentor was really valuable for your leadership. What made that relationship so effective?

Listen fully to their response. Since you’ve thought through the tradeoffs, you know mentors can be great, but they can also be hard to come by and that mentoring relationships take time to develop organically. So, you know the next best question to ask:

• “It sounds like they helped you by ABC. How did you meet your mentor?

When your manager responds with their story about meeting their mentor, you keep digging:

• “Wow, what a fateful meeting that connected you two. It sounds like you built your relationship over time.”

[Pause]

Your manager will likely continue speaking, elaborating on that exact point – that their relationship developed gradually, organically, over time.

This is where you can highlight the gap between what your manager thinks is helpful and what you and your manager have already agreed on that you actually need. Lead with curiosity:

• “I see the value in mentorship. And, last time we discussed how important goals like ABC were to our team’s impact this year, even this quarter. Is that still the case?”

[Pause]

If you identified urgent goals in your prior conversation, the answer here should be, Yes – these goals are important immediately. 

Finally, you can ask for buy-in:

• “I agree that a mentor can be valuable, and, while I’m nurturing potential mentor relationships, what do you think about a coach as someone I could start working with now in a more structured way to help make progress sooner?”

If there’s still resistance, don’t argue—keep digging. Ask:

• “Tell me more. What makes you say that?”

Repeat, repeat, repeat, until you and your manager flesh out their objections and agree on the evaluation criteria. Remember, if there’s resistance to your approach, surface it early. Aligning on the criteria before you invest significant time developing your plan will save your hours of time and energy. 

The Takeaway

This is just one example of one objection and how the conversation can go. The point is, this approach can help you and your manager align on the evaluation criteria, so you then have their blessing on your approach before you invest hours of time talking to coaches. 

Most people falter when faced with objections because 1) they haven’t understood evaluation criteria tradeoffs or 2) because they’re scared of hearing an objection. 

Asking for what you want takes courage. Remember that handling objections is a necessary step to getting what you want. By preparing your own evaluation criteria and listening deeply, the next best question to ask becomes obvious. Asking will feel less scary, because it’s the necessary step to clear the air and help you and your manager align. Practice this, and you’ll meet objections with the artful mix of curiosity and conviction that allows your manager see the gaps in their original thinking for themselves. It’s infinitely more powerful than you simply telling them. 

2. The Goings On

If you grew up in an Asian family and waited for someone to give you praise in order to feel good about yourself…you might still be waiting.

That’s a joke. But only kind of. May, Asian American Pacific Islander Heritage Month, is coming to a close, and I spent the time speaking to AAPI groups. We started the sessions talking about the inner critic, that nagging voice that makes you second-guess yourself. We exposed the sneaky ways it gets in the way of our influence. We left the sessions with a new way to embrace our executive presence and lead the way we want.

It continues to delight me to see people surprise themselves with the strength and clarity that emerge when they have the courage to tap into their inner resources.

Of all the growth I’ve worked on over the years, tackling my inner critic has been the most tender and powerful. Part of the journey has been accepting the aspects of Asian cultural norms that shaped my inner critic. Part of the journey has been awakening to the choices I have to take matters into my own hands – to quiet the inner critic, tune into my inner radio, and let me, the real me, out.

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