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#363: How to Know if it’s the Right Time to Hire a Coach?

If you've ever wondered, “Is now the right time to hire a coach?” listen in, because this episode of Be a Better Lawyer breaks down everything you need to know.

In this episode, I’m pulling back the curtain on what coaching actually is (and isn’t), how to know if it’s time to get support, and how to make empowered decisions that aren’t driven by fear or other people’s opinions.

We’ll talk through:

  • Why you’ll never feel totally “ready” to hire a coach — and why that’s not a problem
  • The mindset shifts successful lawyers make to stop struggling
  • How to evaluate whether coaching is a smart investment for you
  • How to handle financial conversations with a partner from a place of clarity and decisiveness

Whether you’ve been thinking about coaching for a while or you’ve just started exploring it, this episode will give you a process to think about what you want.

🔗 Learn more about coaching by booking a Strategy Session with me.

📧 Want me to answer your question on the podcast? Email me: di**@*********do.com

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law firm growth, law firm audit, coach for lawyers, business coach for lawyers, be a better lawyer, dina cataldo

When is the Right Time to Hire a Coach?

Today we’re answering the question: when is it the right time to hire a coach? The answers I have for you may surprise you.

Hello, my friend. I got this question from a lawyer, and I wanted to answer it here on the podcast. If you have a question that you want me to answer, email me at di**@*********do.com, and I’ll answer it here. Trust me, if you have a question, other people have it too, and it could really help someone out.


Let’s talk about what coaching actually is before we dive into when to know it’s time to hire a coach.

I loved this description of what coaching is: it’s like you walk into a dark room and a coach turns on the light, so you can see. They help you see blind spots. They help you see things you could bump into and fall over if you’re not on the lookout. They help you understand how your approach isn’t getting you the results you want and gives you a new approach. Coaching is really about creating a transformation within yourself by helping you think differently and take actions aligned with the result you want.

Coaching is NOT about telling you what to do. I will say that in my particular style of coaching, I will let my clients know what they can expect if they keep following down a path. For example, if they continue avoiding difficult conversations with people in their practice, and I help them then address what’s happening within them that’s causing them to avoid conversations. Then once we’ve cleaned that up, they can have those difficult conversations and release all the anxiety and stress that avoiding those conversations has created.

Coaching isn’t therapy, but there are times when my clients feel like it’s therapy because sometimes an emotion needs to be processed before they can take action. This especially shows up with my clients who want to be more visible in the marketplace—whether it’s on social media, podcasts, video interviews. It feels incredibly vulnerable doing that, so we process the fears and anxieties associated with growth so they can grow their practices.

Coaching really helps you think differently and take new actions, so you can get the result you’re looking for.


Okay, so when do you know it’s the right time to hire a coach?

Well, the title of this episode is a bit misleading because I will tell you there’s never a “right” time to hire a coach.

When I hired my first coach, I didn’t have a budget for a coach. I don’t think anyone ever has a budget for their first coach. It’s only after they see the results they get from a coach that they think about putting money aside monthly to keep going with a coach.

There was also no time in my schedule for a coaching call. I had to make that time happen. We make time for what’s important to us.

And I definitely didn’t feel ready.

There was also no “feeling good” about investing in a coach. Yes, I wanted a coach, but our brains are designed for protection, so investing money in a coach automatically feels scary. Every time I hire a coach, my stomach twists a little. I know that’s normal, but a lot of people don’t. They take that as a signal that they need to stop. I just know that my brain is sending a signal to my stomach that I’m nervous. And that nervousness and fear are signs that I’m about to expand my capacity. I’m about to expand myself into the version of myself that has the result I’m looking for. We’ll talk more about this in a little bit because I also know I have a budget, and that’s something you likely think about too.


Questions I Ask Myself When Considering Hiring a Coach

1. How long am I willing to struggle in X area?

For me, I’ve focused a lot of my coaching on growing my business, but when I first started with a coach, I spent time learning how to manage my mind around stress and time better. That’s what I do with my clients starting out whether it’s in 1:1 or in my Time Peace for Lawyers group program. Mind and time management is foundational for growth, and if you don’t have that dialed in, then you’re going to struggle growing.

Something I used to think was “I should be able to figure this out myself,” or “it’ll get better eventually” — but that mindset often keeps us stuck way longer than we need to be.

If you don’t get support, the risk isn’t just staying stuck — it’s reinforcing the identity that you have to do it all alone, which becomes its own prison.

Let me get back to the question “how long am I willing to struggle in this area?”

Story about the somatic therapist who fixed my back. I waited a month to have him look at it because I’d never been to one before, and I didn’t really know what he could do for me and because I was cheap. I didn’t want to fork out what I thought was a lot of money at the time for a problem I thought would go away on its own. Instead, I became more miserable and had a difficult time focusing on talking to friends much less work.

So I suffered for a month or more. And looking back it was ridiculous what I let myself go through. Now instead of months, I wait a few days to see if it improves then I get an appointment with Lino. Vastly has improved my life.

I never want to put myself in that position again where I’m struggling when there’s a solution out there. So if I’m struggling in any area of my life, I recognize it. I don’t beat myself up and tell myself I should be working harder or I’m lazy or anything like that. I wouldn’t say that to myself if I was in physical pain, so I definitely won’t do that in mental pain. That just contributes to the mental suffering. Instead, I seek out a coach.


2. I anticipate problems and ask myself what will help me make those problems easier?

This year I’m working towards doubling my income in my business — a super audacious goal — and I know that’s not an easy thing. I know there will be bumps in the road, my mindset will want to go sideways and tell me to give up, etc. I’ll feel fear and doubt along the way. I already know this will happen. I also know that when I feel doubt or fear, I want to freeze. I know my patterns because I’ve been through master coach training and self-coached myself for so long and received coaching for so long. So what I do is anticipate it, and solve for it. The way I solve for it is by getting help. I hired a couple coaches to help keep my mindset on track and to give me a bit of accountability along the way. They help me check in on my brain and ensure I’m not letting it go sideways when I want to focus on the goal ahead.


Let’s Talk About Money

Now let’s talk about investing because being responsible with money is one thing and letting fear drive my decisions is another.

So the question my brain always asks is, “Can I afford it?” Your brain probably does this too. But is it coming from fear or a neutral feeling? That’s another question I ask myself to ensure I’m not letting fear drive the bus.

The question “Can I afford it?” is a tricky one because I don’t want to work from my circumstances. When we work from our current circumstances, we can’t get out of those circumstances.

Working from circumstances is like sitting in the backseat of your own life, letting other things and people (like clients, your calendar, your inbox, your number in your bank account) decide how you live. And you’re just hoping that you end up somewhere good. When you stop working from your circumstances, it’s like moving to the driver’s seat of your life. You’re taking the wheel and taking yourself where you want to go.

But if I’m tired of struggling and I know there’s going to be problems along the way, I don’t want to be constrained, but the truth is, it’s the responsible thing to do to look at our finances.


How I Look at Coaching: As Both Buyer and Seller

I look at the result I want and what is it worth to me to have that result in my hot little hand? For example, if I want to double my business, how much is that worth to me? 10% of that goal? 15% of that goal? Honestly, I’ve invested more than my goal because I didn’t have the skills I needed to build my business in the first place, but that’s not always available to people.

I’ve used credit cards because I wanted my goal so badly. I’ve taken funds out of my retirement account because I wanted my result so badly. I’m not saying you should do this, but that’s me. I’ve developed the ability to take more calculated risks over time. It was scary every step of the way, but that’s how I step into a new version of me over and over again. I meet the fear, know it will be there, then I make a calculated risk asking myself whether the result I want is worth X amount of dollars.

When lawyers book strategy sessions with me, we talk about the value of what they’re going to be getting and what they think about it, so I help talk them through their thoughts. I’m not telling them what to think at all, I’m simply a neutral sounding board for what they’re thinking.


What I DON’T Do As a Buyer

I don’t ask for other people’s opinions or permission.

Sometimes we think a spouse or a friend can help us make a decision, but ultimately, they don’t know what’s valuable to you and why. Only you know that. And when we defer our decisions to someone else, we then make our decisions and our life experience someone else’s responsibility.

When you talk to spouses about financial decisions — whether coaching or anything else — I go into those conversations having an opinion and knowing what you want your spouse to say.

If you want them to say yes, what would you do if they said no? Would you immediately back down or would you give them a laundry list of reasons why this is the decision you’re making and ask for their support?

Would you be willing to make the decision you want to make whether or not you had their support? If so, why? If not, why?

I could do a whole podcast just on how to talk to significant others about financial decisions, so if you want to hear that podcast and have questions you want me to address, email me at di**@*********do.com and I’ll make that for you.

Can I Afford NOT to Do It?

What will I lose out on if I don’t get help? That loss can be in terms of time, money, or mental energy.

For example, if you have an assistant but you’re not delegating work to them, you’re losing time and money. I have a lot of clients who fall into this trap, and we work together to get their time and money back. They also get their mental energy back because they learn HOW to delegate without micromanaging to maintain their peace of mind over the work product they’ll get back.


As a SELLER of Coaching

I know not everyone can afford to work with me 1:1, which is why I created Time Peace for Lawyers. In Time Peace we talk about everything from how to use a calendar the right way for your practice, how to delegate, how to create boundaries, we coach on prioritizing, and so much more.

I have spots open in both my 1:1 and in Time Peace, so you can go to my website to learn more: https://dinacataldo.com


Other Things I Think About as a BUYER of Coaching

1. I want to get to know my coach.
The more I know them, the more I can get a feel for whether I’m going to get what I need from them. I’ll usually gain these insights by listening to podcasts or being on their email list. Then I get insights into how they think differently from how I think. Because people who have the results you’re looking for think differently. I want that person because they’re going to help me retrain my brain to think differently when we work together. I might also join a lower price point program they have to see if I like their style.

Time Peace is a great opportunity to see if you like my style of coaching, AND you’ll have an opportunity to sign up for single one-on-one sessions during Time Peace. I offer those at a special rate because you’re a part of Time Peace. I never do anything like this outside of people who are members of my programs, so if you’re not sure 1:1 coaching is for you or you can’t afford 1:1 coaching right now, joining Time Peace is another way you can get access to coaching.


2. I want to know that I’ll be supported — and pushed.
I want that kind of push because it keeps me honest about my goals. It keeps me challenging my brain to think differently.

That’s why in my 1:1 program, I offer additional support for lawyers who are growing their business and challenging themselves to do new things. I do this with Voxer coaching — Voxer is a free app that lets you contact me at any time to ask questions, get coaching, and celebrate your wins anytime.

I also give my 1:1 clients access to a library of Business Strategy Calls that cover everything from how to do a webinar, to how to become more visible in your business, to how to hire employees, and more.

One of the best pieces of advice I’ve ever received was to “stay in the material” when you’re challenging yourself to do something new, so I give my clients access to those supports to help them stay in the material.


3. I commit to doing what the coach suggests.
I never want to invest my money and poo-poo what the coach says — the coach who I’ve vetted and decided I want to work with. The value of coaching isn’t in just listening — it’s in implementation. Coaching only works when you engage with it, try things out, and allow yourself to be uncomfortable while growing.

As an aside, sometimes lawyers tell me they don’t think they’re coachable. You’re coachable if you’re willing to try things, even when they feel uncomfortable. If you’re open to the idea that your way of thinking might be part of the problem — not because something is wrong with you, but because every result you want requires a different mindset.


4. I promise myself that I’ll ask for help — even when I don’t think I need it.
It’s common for our brains to lie to us and tell us we should be able to figure it out ourselves or that this question is dumb. It can be uncomfortable showing vulnerability, especially in a profession where we’re taught to look like we have it all figured out.

Putting my coach hat back on — I do Zoom calls with video on intentionally for this reason. A lot of lawyers are afraid to ask questions or are struggling with something, but they stay silent about it. It’s easier for me to see where this is happening when I see lawyers. Most of us have horrible poker faces. But I also can read the energy of the person on the other side of the call. It’s really interesting because more often than not I will know exactly what’s going on with the lawyer getting coached, and that was exactly what they weren’t speaking up about.

You probably do this all the time, and that’s why so many of us like to have in-person interactions — so we can read the other person.


Quick Recap of What We Covered

  • There’s never a perfect time to hire a coach — you won’t feel “ready,” but that doesn’t mean it’s not the right move.

  • Coaching helps you see blind spots and take aligned action, so you can stop spinning your wheels and finally get real results for yourself and your practice.

  • If you’re struggling, ask yourself how long you’re willing to stay stuck — you don’t need to stay stuck or wait for things to get worse. Be honest about what you’re willing to endure.

  • Don’t let fear or your current circumstances drive your decisions — get in the driver’s seat of your life and law practice. Don’t ask for other people’s opinions. And go into conversations about financial investments having a strong opinion first and know what you want to get out of the conversation.

  • Coaching isn’t about listening passively, it’s about implementation — that’s how transformation happens.


If this episode brought up something for you — whether it’s a place you’ve been stuck or a goal you’re finally ready to pursue — I want to invite you to book a Strategy Session. We’ll talk about what’s getting in your way and how to move forward. Because you don’t have to stay in the backseat of your life or your law practice — you can take the wheel.

You can book a Strategy Session or join me for the next round of Time Peace at dinacataldo.com

I hope you have a fabulous rest of your week, and I’ll talk to you soon.

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