The 5 big questions you should consider (and 7 you shouldn’t)

I’m in quite a good position to write this particular blog. As well as being a full-time business coach since 2011, I’ve also been lucky enough to have been coached (both informally and as a paying client) by several.

Some of these coaches you may have heard of and some probably not – all of them were seriously good.

But the interesting thing is what happened next, because some of them got the very best out of me … and some didn’t.

The comment about them all being seriously good is not a platitude. They are highly regarded in the peer group, so this isn’t as simple as ‘how to hire a great coach’.

It’s a question of how to hire the right coach for you – and that’s much trickier.

There are 5 questions you should consider.


Do I want a coach who Challenges me or Supports me?

The long version is that everyone has an ideal amount of pressure required for them to perform at their best.

How much is ideal? It varies from person to person.

Too much pressure leads to people freezing – or ‘choking’ as it’s known in sport. Too little pressure leads to complacency or laziness.

The short version is that some people need a bit more KUTA (Kick Up The A***) in their lives and some need a cuddle. It’s the stick and the carrot.

This is the one where you will need to really stop and think about it. Ask the people who know you best what they think. Remember past teachers / friends who have had a positive impact on you. Think about people who have wound you up and triggered a negative reaction.

Take it from me, what you ‘project’ may not be what you need.

If you’re the type of person who can get complacent and are not overly sensitive / emotional, you may well find a ‘Supporter’ style coach guilty of colluding with your excuses and (relative) underperformance.

If you already put yourself under plenty of pressure, you might well find a ‘Challenger’ style coach very stressful and potentially even damaging.

Good coaches are adept at tweaking their style to the personality and mood of their client – but they will have a default tendency that they lean towards over time.

The proof of this pudding is not how you feel on the call – but how you react after it.


What experience do I want my coach to have?

The question I get asked the most concerns my experience of coaching that type of business.

The most precise version of this I’ve ever come across was “have you ever successfully coached a high-end, West London-based male grooming business before?” Seriously. Thank goodness he didn’t throw his star sign, height and hair colour in there or I might have struggled.

I’ll leave the debate about the merits of hiring a coach with direct and specific experience for another time – because it is debatable.

What is definitely worth factoring in is the experience of your prospective coach in your type of business – ie B2b / B2C / Face to Face / Online / Repeat / One off. This will have a big impact on Sales & Marketing, and you’ll want to be confident that your coach is confident in your area. If a coach has successfully coached a plumbing business, there is every reason to expect they’d be good with an electrician or painter. Similar customers, similar marketing channels, similar sales process.

It’s also pertinent to ask about the size of business they coach the most. The challenges you’d face within a team of 30-50 people is very different to say 3-5. The chances of a solution not working in the first iteration only go up with the size of team, so you’ll want someone who’s prepared for this and ready to coach you through it.


Do I want a coach who is the same as me – or the opposite?

You need to decide if you want a coach who is strongest where you are weakest – or who matches you strength for strength.

The benefits of having someone who is strong where you are weak (eg detail, or long term vision, or structure) is pretty clear: they’ll find it easier to spot what you miss.

The knock-on effect of working with such a coach is that you might find the session ‘hard going’ and see it as a chore rather than the highlight it should be.

This all comes down to psychometric profiles which I’ll cover in another blog, but for now think of it this way:

  • If you are an optimistic type who’s big on emotion – you might find your opposite cold, picky and slow.
  • Whereas if you are a calm, measured empathetic type, you might find your opposite an arrogant bully.
  • If you’re the detailed, structured, logical type, you might find your opposite woolly, vague and insincere.
  • And if you’re the dominant, results-orientated self-starter, you may well find your opposite ‘wet’.

To my mind this is the least important of the 5 Questions for a simple reason: seeing into blind spots is to a large degree enabled by having proper KPIs (Key Performance Indicators) on a RAG (Red Amber Green) Dashboard – and any good coach will be able to walk you through best practice for that.


What business values do I want to find in my coach?

A value is something that influences how you see the world and prompts you to behave in a certain way.

As such, the Values your coach has will influence how they see the world, business in general, your business, your team and customers – and also your challenges and opportunities.

It will influence their view of what is possible in your industry … and what you’re capable of.

Of what’s right, what’s wrong – and what’s debatable.

You want someone to help you maximise your potential and build the business of your dreams. And when you achieve that you will want to feel a sense of pride in how you’ve gone about it. Questions of reputation and legacy.

A coach with values you share is more likely to be help you keep to a path you look back on with pride.

Also, you will never get full value from your coach unless you are ready, willing and able to be completely honest with them about what’s holding you back and this is tough to do unless you really respect and trust someone. And that’s tough to do unless you share similar values.


Do I want a Transactional Coach or a Transformational Coach?

This might seem an odd one to make such a short list – but it’s probably the biggest question.

There are only 3 rules that hold true for every owner of every business. The first and most important is ‘Be X Do = Have’. Ie that your results (Have) are a function of not just your actions (Do) but also your and approach (Be).

Some coaches I know lean so far towards the ‘Be’, they are like a cross between Yoda and Buddha. They are in the purest sense, closer to being Life Coaches.

Some are more like Lord Sugar and are very black and white – prescriptive and granular. They are in the purest sense almost consultants.

Yoda Coach will tell you that your Beliefs trigger your Thoughts which trigger your Actions which cause your Results. They’ll tell you that building a ‘To Do List’ without addressing Thoughts and Beliefs will only generate a bigger helping of what you had before – which may well not be palatable.

Sugar Coach will tell you that positive thoughts won’t pay the mortgage. They’ll tell you that doing stuff causes results and you feeling more positive so why waste time with Affirmations when you could be getting stuff done? They’ll believe that if all they do is hold you accountable to doing what you said you would, that you’ll get results more than enough to pay the fees (and there is some truth in this).

So which one is ‘best’?

Experience tells me that Transactional Coaching yields steady if unspectacular results whereas a shift in attitude or belief can yield a step change in ideas and performance.

You’ll have your own preference.

My view is this is one of those times where the ideal lies exactly halfway between the two.


These are the factors that didn’t make my Top 5 List – but might make yours:

I haven’t mentioned some things that you might well think are important. It’s simply that on reflection they’re not big factors – for me.

Gender / Class / Race / Religion: If it’s not an issue for them it’s not for me either. I don’t care if other people do or don’t swear, for example – but I get that you might.

Fees: If they’re the right coach for me I’ll find their fees – and get a RoI from them.

Location: Face-to-face is nice but I find travelling for work a bore: overall, I’m fine with Zoom.

Humour: For some people it’s important to get on with people they work with but be very careful with this. You don’t want coaching to be too friendly and fun – that way lies collusion.


In conclusion

If you answer these honestly you will have a short-list of coaches who have the potential to be a long-term partner in your growth.

From there, all that matters is, well, growth.

Remember, growth or results in a business context are a function of Clarity + Emotion + Action.

So, a great business coach for you will be someone who helps you achieve a sense of perspective. They’ll stoke your confidence and impel you to learn about the next challenge ahead. If they then hold you accountable to your approach and actions, you will get results – by the hatful.