20 Must-Ask Questions Before Hiring a Coach or Consultant - EP 026

In this follow-up to Episode 25, "The Hard Truth About Hiring Coaches & Consultants," we dive even deeper into how to make smart, informed decisions when choosing a coach or consultant for your business.

Last time, we discussed the challenges of hiring a coach or consultant in an over-saturated market, the rise of buyer skepticism, and the importance of understanding the difference between price and value. We uncovered some of the pitfalls of high-ticket coaching programs and how to navigate the complexities of finding quality support.

In this episode, I’m sharing 20 Must-Ask Questions Before Hiring a Coach or Consultant. Whether you’re considering a business coach, mentor, strategist, advisor, or even a service provider, these questions will empower you to assess whether they have the experience, skills, and compatibility to meet your needs and help your business thrive.

These questions are divided into four key categories:

1. Experience and Qualifications: Learn how to gauge their expertise and understand if their past work aligns with your business needs.
2. Skills and Approach: Get insight into their specific skills and coaching style to determine if it fits your learning style and goals.
3. Insights and Wisdom: Evaluate their strategic thinking and depth of understanding, ensuring they can guide you with a broader perspective.
4. Personality and Culture Fit: It’s important to feel aligned with the person you’re trusting with your business. These questions will help you figure out if they’re the right match for you, personally and culturally.
5. Goals and Expectations: Understand how they measure success and ensure their approach aligns with your desired outcomes.

By the end of this episode, you’ll be equipped with all 20 questions that will serve as your checklist for making sure you’re making the best investment for your business. 

Key Takeaways:

• Asking the right questions before hiring a coach or consultant is essential to making informed, confident decisions.
• Experience and qualifications are crucial, but it’s equally important to find someone whose personality and values align with your own.
• Consider their specific skills, insights, and wisdom, and make sure their approach matches your business needs and personal style.
• Use this checklist of 20 questions as your guide to confidently navigate the coaching and consulting space.

Here’s the link to get this list of questions for free, so you’re prepared before your next consultation or discovery call: https://bit.ly/must-ask

If you’re ready to have a deeper conversation about how to maximize impact, profit and pleasure in your business and life, you can schedule a time to connect with me right here >>> 

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Episode Transcript

Hello and welcome to Pleasure and Profits. I'm your host, Rachel Anzalone, and this episode is a follow up to the previous episode, number 25, called The Hard Truth About Hiring Coaches and Consultants. In that episode, I discussed the challenges of hiring a coach or a consultant in a saturated market, which is the case right now. I talked about buyer skepticism in this current market, some common pitfalls of high ticket coaching programs, and the importance of discerning between price and value. That episode is all about how to navigate the coaching and consulting space and make informed decisions when investing in support for your business. In this episode, as a follow-up, I'm sharing 20 must-ask questions before hiring a coach or a consultant. 

And let me tell you, my plan was 10 and there are 20 and some of them have...like sub questions in them. So I'm going to go deep here into some of these they're definitely good food for thought for you to consider. 

And if you are a coach or a consultant yourself, they’re questions that you should be prepared to answer for your customers as well, and will help you get a better understanding of who is the right fit for you when people are looking to hire you to support them in their businesses or in their life as well. So at the end of the episode I will share with you a link where you can go find the list of questions for free. You don't even have to enter your email address. You can just go straight to the document. You can download it. You can copy and paste it. Do whatever you want with it. So I'll share that link at the end. These questions are really designed to help you assess the experience level, the skill set, and in particular if this person is a right fit for your needs, for you, and for what you need in your business at this time.

Okay, now let's get into the questions. Starting with experience and qualifications. Number one, "What is your background and experience in coaching or consulting?" And so it's not that there is a specific level of certification or experience that is required to hire someone, but just that you know that you're going into a coaching or consulting relationship, aware of what experience this person has. You might interview someone and they might say, you know, I'm brand new to the coaching industry. However, I have years of experience having done this type of work at companies, in other roles that I've had. And then you can discuss and get into what the nitty gritty is of their experience. But you definitely want to know where they're coming from. If they have training, if the training is relevant, it may be training is not relevant you. Maybe it's all about life experience and work experience so you can collect that information and make an educated decision there. 

Number two, “Can you share your experience working with purpose-driven businesses and how it informs your approach?” So there is a huge difference between coaching and consulting to support heart-centered, purpose-driven, soul-aligned entrepreneurs than there is supporting somebody who is selling widgets or, you know, doing some kind of mass market service there's just a different approach and so you want to make sure you're working with somebody who's going to get who you are, where you're coming from, what your mission is, and that they have experience working with people like you, businesses like you. 

Number three, “Can you share specific examples of clients who you have worked with who have similar businesses to mine and or who have faced similar challenges to mine? And follow up to that, can you share specific results that you help these clients achieve?” And so you might find that someone can give you sort of general information here, but you could follow up with a question of asking them if they have any documented case studies or testimonials as well that they can share with you. And so we're looking here for specific examples of similar businesses, right, and similar challenges. And they don't necessarily have to name names. There might be some privacy issues, but they certainly could give examples and ask them to describe and to go into detail, not just say, I worked with this person, this person, this person, or naming businesses, but really what did they do in those places and how did they support. 

Number four, “How do you stay updated on industry trends and best practices?” So if we're about strategy and tactical that could be really, easy to assess if that is, you know, enrolled in educational programs, or they're researching, they follow other leaders in order to stay on top of what's happening and what's current from a tactical or strategic perspective. But this might also be as simple as like, have you received any trauma informed coaching training? Or is there some other aspect of you personally that you want to make sure that they're up to date on in terms of challenges that you have. Are they current with what's happening? Or are they sharing practices and processes that maybe worked 10 years ago but don't necessarily work today in the current market?

All right, moving on to skills and approach. Number five, “What is your coaching or consulting philosophy and who have you learned from that informs your philosophy?” I think this is a really valuable question. It's one that I wish I had asked many, many times in the past. Not the question about what your coaching or consulting philosophy is, but who have you learned from? Very recently it occurred to me as I'm educating myself through books and exposing myself to different coaches, different strategists, etc. if I look back at other coaches that I've hired or worked with in the past, that I can see where that information came, where it was filtered through. And I can understand now what somebody said to me five years ago. I can understand it better now because now I'm reading the source material for that coach. And if at the time I had asked them who they learned from, and I had gone deeper with those sources then, I could have gotten so much more out of that coaching experience. 

And I think we have a tendency to think that, either like we don't want to reveal our sources something like that like “Why would you hire me if you can go straight to the person that I learned from?” I think that's you know, it's kind of a normal in our culture response and simultaneously it's very much based on scarcity, right and that we're like competing with our teachers which is kind of absurd like there's enough to go around and the other side of this is that I think as a consumer, sometimes we think it might be rude to ask where somebody learned something, that we're sort of supposed to act as if every idea they have is an original idea and almost never is an original idea. Usually, anyone who's teaching something is teaching a conglomeration of things that they have learned from lots of sources that they have then filtered through their own lens and to ask the source of some of that stuff is not inappropriate and can really be incredibly beneficial.

Okay, number six, “How do you customize your approach to fit individual client needs?” Pretty straightforward. Number seven, “What methods or frameworks do you use in your work with clients?” And so they may not want to be able to share specific details of their methods or framework, but they should be able to give you a sense of what they're doing or what they're working with. And so it's going to give you an opportunity before you get engaged, to really see what this person's process is, what their approach is, and whether or not it's a good fit for you. For example, if I meet with a prospective coach or consultant and I ask them what methods or frameworks, and they're very focused on a 90 day sprint, then I know they're not a good fit for me because I don't want to be in a sprint. I want to be in a slow, steady, consistent, show up everyday, do the work, make progress, not in some time-bound deadline that feels frantic and intense. So I can make that choice if I ask that question upfront. 

All right, next section, insights and wisdom. Number eight, “How do you help clients navigate obstacles or setbacks in their journey? How do you help clients navigate through the challenging times that they're having?” Do they have the skillset, the experience to actually help people who are not progressing as planned.

Number nine, “What are some common fears, doubts, pitfalls, et cetera, that you see heart-centered entrepreneurs making and how do you help them overcome these?” Because chances are, we probably all have a little bit of those same fears, doubts, et cetera. And how do they help people overcome those so that you can get an understanding of how they might help you overcome those same challenges. 

Number 10, “How do you integrate your personal values and mission into your coaching or consulting practice?” I think this is really important and it's definitely become more more important to me that I want to be working with people who share my values. And it's not such a clear line of distinction in this space that we're in, in a world of heart-centered entrepreneurship, purpose-driven entrepreneurship. There isn't this clean and clear distinction of our separation between personal and professional. And it is part of the work that we're doing is the intermingling of these two things. And so what someone believes, practices, enforces, encourages in their personal values is certainly going to bleed into their professional work. And you need to be able to make an assessment if you feel like those values are in alignment with your own and whether or not that coach or consultant's mission and objective is in alignment with your own.

Okay, next section, personality and culture fit. This is where the majority of the questions are. I think more often than not, we can hire someone that has the skills, that has the experience, that's often very easy to see in their website, from their testimonials, from referrals, and often where the breakdowns happen is in personality and culture fit. And so this is where it gets really important to ask the deeper questions. 

So number 11, “What values are important to you in your coaching and consulting practice?” This kind of plays on the question before, which was about integrating your personal values into your coaching and consulting practice. But as a coach or consultant, what values are really distinct and important to you.

Number 12, “What does your ideal client look like?” This is really important. Ask them if they work with somebody already who they feel like is an ideal client? Ask them to describe that person in detail and why that person is an ideal client for them. And then ask them if they think that you fit that description as well. And if they do, ask them why. Ask for details.

Number 13, “What does your ideal client relationship look like, especially in terms of trust and collaboration?” This is an opportunity to really see what motivates them, what's going to keep them connected, what's going to drive them to help you deliver the results that you're looking for. What does that collaboration and trust and communication look like? And follow up to that.

Number 14, “What are your expectations for client commitment and engagement?” These questions are so important. I don't even want to guess a percentage, a very high percentage of times that things don't work out when somebody hires a coach consultant, et cetera, is that there has been a mismatch in expectations around what the client is expected to show up and do and communicate around and what the coach or the consultant is expecting to show up and do or communicate around. And so this is a very clear question to ask. If I hire you, what are your expectations of me? And then I can assess, can I actually meet those expectations? If part of the expectation is that, I'm present on a certain number of calls per week or that I'm delivering deliverables to you so that you can then take them to create the strategy, you know, to go do the work. Do I actually have the capacity to do that? Those are really important things to know ahead of time.

Number 15, “What client behaviors or mindsets do you find challenging to work with and how do you address those situations?” This also is a really great question to really get a handle on. Maybe what triggers this person? What are their pet peeves? How do they deal with challenging situations? The next question is going to touch on that too. What do they find challenging to work with and what's their method of dealing with that?

The follow-up question to this number 16, “Can you share a specific example of a challenging client situation you've encountered in the past? How did you handle it? What was the outcome?” So this is a question that's pretty standard on any kind of job interview And I think it's completely appropriate to ask this question of somebody that you are hiring in to support you in your business. How do they handle this stuff? If they have a challenging client situation, if they don't see eye to eye, if somebody's dropping the ball, do they ghost? Do they disappear? Do they address it head on? Do they get confrontational? These are really important questions

Number 17, “What's your communication style and how often can I expect to interact with you?” Again, super important to know whether or not the way this person operates is gonna fit in with you and your business and what your style is.

All right, moving on to the next section, goals and expectations. Number 18, “What metrics do you use to measure success in your coaching or consulting engagements? And how will we measure if we're on track in terms of timing and deliverables?” It's one of those things that if this information isn't nailed down and there isn't a clear process for measuring, that it can feel really ambiguous and there can just be a misunderstanding. One person thinks you're completely on track. The other person doesn't really know if you're on track and getting that information up front is incredibly important. 

Number 19, “How do you handle it when a client is dissatisfied or doesn't achieve expected results?” What happens if I hire you as a consultant in my business and I don't get the results that I'm looking for? Now, this can be a little bit tricky because so often, maybe even 100 % of the time, in order to achieve results, both parties have to be engaged. It has to be a partnership. Nobody's delivering a result for you solo. It doesn't even matter what it is. It could be as simple as a service provider, a graphic designer providing a product for you is going to require that you deliver certain things to them and that you communicate with them and that you give them the tools and the resources to be able to execute that job. And so it's always a partnership. And so the question around how do you handle it when a client's dissatisfied or doesn't achieve expected results can really help you get clarity on is this person going to disown the project or the responsibility? Are they going to take responsibility? Are they going to want to have a conversation about like, okay, maybe my team dropped a ball here, but here's where your team dropped a ball or here's the thing I needed from you that I didn't get. And that's why we didn't get to this point. How is that going to be documented? How's it going to be handled? And ultimately, are you going to get what you're looking for at the end of this engagement? Or, is there a high probability that you're going to walk away dissatisfied? And not just dissatisfied with the product, but dissatisfied with how your dissatisfaction was then handled.

And finally, question number 20, “What is the typical duration of your coaching or consulting engagements?” There's no right or wrong answer here. It just gives you the ability to make an assessment whether or not somebody says, you know what, I actually, I usually try to start out with people in a three month engagement. And what ends up happening is that they're really happy with my work and they want to keep me for six months or nine months or a year or two years or three years and I have these ongoing engagements. That's brilliant. Or it might be that they're delivering something, an experience, and they may say, I work with people in a three month and then we're done. And then I like to let people go and see how they work with that for a period of time. And if we want to talk about working together again in the future, we could do that. So you have an understanding of what sort of the way is that they approach those engagements and if their intention is that it's a short-term or long-term thing, regardless of where you're starting.

Okay, so I know that's a lot. It's 20 questions. Some of them have sub-questions. It's probably more like 25 questions. It's not that you have to sit down and grill somebody through these questions in order to determine if they're a good fit for you. You might through reading their materials, through looking at their website, through seeing testimonials, through the referral, if they came through a referral through those conversations, be able to kind of check some of these off and gather some of this information along the way. However, they're definitely good questions to consider and to assess, do I need to know this answer or not? Is a positive or negative response to this going to impact how this relationship goes, how this engagement goes, the result that I'm going to get from this? And I don't think these things are to be taken lightly. In the last episode, I mentioned you wouldn't go into a car dealership and have a 5 minute, 15 minute, even a 20 minute conversation with a salesperson and then just sign over 20 or 30 or 50 or $100,000. And yet.

This happens all the time in the coaching and consulting, and particularly in the online business space where there's a 20-minute discovery call. And at the end of it, you're supposed to, as a buyer, commit to a massive investment, sometimes in the realm of 10 or 20 or 30 or $50,000 or more. 

And before you do that, don't you feel like you should ask some really clear questions? Don't you feel like it's your responsibility as a business owner to determine if you're making a good investment or not?

And sometimes I think we don't ask those questions because we don't want to seem like we're not ready, we're not confident, we're not sure. You know, we're talking to somebody who we believe has some level of expertise that we don't have and we want to seem like we have it together. And the best way to demonstrate that you have it together is to ask all the really critical questions. 

And so just a couple of more things that I recommend you make sure that you get in writing are fee structure, a documentation of what's included, number of sessions, length of sessions, deliverables, communication expectations, turnaround timelines, project timelines, get a commitment of what exactly it is that you're paying for. And then also, what's the cancellation or rescheduling policy if there needs to be a delay for some reason or other, whether it's just rescheduling a session or it's putting an entire project on hold for a period of time, what's their policy around that? And get that in writing as well. 

Okay, there you go. Those are my 20-some plus questions. If you want to grab this list for yourself, you can go to the link that I'm about to share and you can download it, you can copy and paste it. Save it to your own drive, share it with your team, your friends, your peers, whatever you want to do with it. And you don't even have to enter your email address, nothing. This link will take you directly to a Google Doc with this information in there. And the link to the list is, it's a bit.ly link. So it's bit.ly/must-ask

I hope that you will grab the list. I hope you'll use it next time you're considering hiring a coach or strategic support and that it helps you find the right for you support that aligns with your values, your goals, and meets your needs for where you are in this moment of your experience. 

Thank you so much for being here until next time. I'm wishing you even more pleasure and profits. I will see you soon.