What Should I Consider When Hiring an Advisor, Coach, or Consultant?

Helpful check-in questions for small business owners hiring professional/business development support.

Use this when hiring someone new or when you have doubts about someone you’re currently working with.


The three main things I’d consider are:

  1. The change you’re seeking

  2. The practitioner’s style/approach

  3. How you feel and who you’re able to be around them


First and foremost, what’s prompting you to want to work with someone?

What do you want help with? What is the change you’re seeking?

  • If you started working with this person tomorrow, how will you know it’s been a success 3, 6, or 12 months from now? What changes will you notice in your business, your team, or yourself?

  • Do you need help with the vision (what do I actually want, what are we building… etc.), the how (what are the practical structures and actions….), or figuring out why you’re not moving forward on what matters to you (we keep falling into the same patterns, I keep avoiding…)? Perhaps some combination? Or someone who focused primarily in one area but has the capacity to honour all of them?

It’s OK if what you want evolves. Initial direction helps you focus your search.

I’ll also say—a good practitioner should be able to help you clarify this on a discovery call without pushing you to work with them.


Second, make sure the practitioner’s approach meets your needs.

What kind of direction do you want? Do you want to be told what to do, do you want help surfacing your own answers, do you want the work done for you, do you want a true strategic/creative partnership…?

How much, and what kind of structure do you want? How do you want to be held? Do you want someone direct and firm? Do you want space to unfold and go on tangents?

This is also where you can dig into due diligence like:

  • Have they worked with people like you? (Your industry, growth stage, social locations… anything that’s important to you)

  • Are they going to teach you how to replicate their business or help you build your own? This one is big!

  • What are this person’s limits? What can and can’t they help you with? No one you hire is going to be a silver bullet. Be mindful of your expectations on the working relationship and be able to discuss it together.

Mismatched needs and unspoken expectations are often what lead to unproductive working relationships. This is tough to suss out and there’s no need to get it perfect out of the gate.

At minimum, I’d look for a practitioner with high self-awareness (aka the ability to name their limits) and the capacity to discuss the sticky stuff. You should be able to ask them uncomfortable questions without them getting thrown off or threatened.


Lastly, and I’d argue most importantly, how do you feel and who are you able to be around this person?

  • What parts of you need to be seen in order to do this work? What parts of yourself are you keen to try on and practice? You should be able to be yourself without worrying about intimidating or destabilizing the person you’ve hired.

  • Can I tell them the truth? If you want to change, you need to be able to tell the truth (aka try on multiple potential truths) with yourself and the person you’re working with.

  • How do I feel before, after, or during a conversation with this person? How your body feels and the thoughts you have will give you a lot of information!

  • Do I feel judged or limited by this person? There’s a real power dynamic when you hire someone to consult/advise/coach you. A skilled practitioner is aware of that, and is able to hold your experience/reality as well as their own. Things get messy when practitioners aren’t able to hold that separation or “dual consciousness”. That’s how projection and judgment happen.

  • When I’m around them do I feel like I have to be more like them, or am I able to become more of myself? This is a big one too!

Change cannot happen without trust, truth, and safety. Look for those conditions in any business partnership.

Work with someone that makes you feel safe* enough to grow.


*Insert whatever word feels true for you here. What do you need to feel to be able to grow? Do you feel that around this person?

You can read more about my approach here.

You can book a free consult call to explore working with me here.


Kate Smalley

Kate Smalley is a small business advisor, facilitator, and educator based in Toronto, Canada. She writes about growth and business development for principled, industry-shaping entrepreneurs.

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