Business coaching: How to ask tough questions and challenge mindsets

Business coaching: How to ask tough questions and challenge mindsets

Posted: Thu 9th Jul 2020

A good business coach unlocks a business owner's potential. They ask challenging questions to help people make better decisions and improve their mindset.

Running coaching sessions is part art and part science. Coaching models provide structure, but everyone's needs are unique. A coach has to understand the person they're working with, challenge the person's thinking and get to the root of the problem.

Here, experienced coaches from Enterprise Nation's community share how they run coaching sessions. If you're a coach, this guide will help you develop or refine your approach. If you're a business owner, it explains how the process works and how to get the most value out of your coaching sessions.

A coach's role

Coaches help business owners improve their mindset and develop and implement strategy. It's a different relationship to mentors, who tend to share their own experiences, and consultants who work on a specific function of a business.

Engagements can be for a single or regular session, such as every week or month. Pricing varies depending on the coach's experience but it's common to pay around £100 per hour and £500 per day.

Preparing for the first coaching session

Understanding someone's business and objectives provides context for the first coaching session. As business coach Dr Carlton Brown, director of Aspire Consultancy, says:

"I'm keen to understand the business. That's key. Their core objectives. Not only what they want to achieve but their value proposition."

It's common for coaches to book a 20-minute or 30-minute session to explain how the process works and understand the business owner's objectives. Chemistry is an important part of the coaching process and the initial chat provides an opportunity to get to know each other.

Productivity coach and Go Do founder Karen Eyre-White says it's useful to talk to new clients about what coaching involves, particularly the difference between the role of a coach and a mentor. She stresses the importance of feeling confident enough to say no to clients that aren't a good fit.

Dr Brown asks their key issues, objectives and pain points by email or phone call ahead of the first session.

Checklist to prepare for a business coaching session

Here are some points for coaches to consider before a first session with a new client:

  • Length of the engagement and individual sessions

  • Cost

  • Terms and conditions

  • Business owner's key objectives

  • How they will run the sessions

What to cover in your first coaching session

Engagements that last more than one session tend to start with an exploratory session, which helps the coach understand the business. This could last from one hour to a day. Every business owner has unique needs but it could cover the following:

  • Goals and aspirations: What do they want from the business? What does success look like?

  • Finances: How is the business performing? What do its cash-flow forecast and profit and loss statements look like?

  • The company's proposition: What is its USP? How does the sales process work?

Karen Eyre-White says:

"My first sessions are quite open-ended. We talk about where they are at the moment and where they want to get to. They then start to fill that vacuum."

How you might run a coaching session

Most coaches work from an agenda. Session topics cover specific challenges like:

  • developing new team roles

  • discussing how a business's proposition will evolve

  • sense-checking a marketing campaign

Making the desired outcome clear will drive progress. Mention it in the agenda, at the start of the conversation and revisit it at the end – how well did the session go?

Dr Carlton Brown starts with an overview of the ground rules. He has an idea of what model he's going to use too, such as GROW (Goal Reality Options Will) coaching, but stresses the conversation needs to be dynamic.

Karen Eyre-White has created a template Trello board with the topics she covers and related resources. She personalises it for each client and updates it as the engagement progresses. That way, she has useful tools to hand.

"Productivity coaching is slightly different. They don't just want coaching. They want some of my input in terms of what I know about productivity. I'm finding a balance between those two things."

That might mean clients show Karen their inbox or she shares planning templates, for example.

Recording session outcomes and actions

At the end of a session, try to summarise the key points covered and actions to take away. This reinforces the progress made and provides accountability. Dr Brown says:

"After the session, we summarise the key actions, make sure the actions are SMART and put timelines against them."

SMART goals are goals that are Specific, Measurable, Achievable, Relevant and Time-bound.

Accountability is a key part of the value coaches provide. Business owners love the autonomy of working for themselves, but it's difficult to hold yourself accountable.

"Committing to an action plan helps. Then we review it. You have to sense check it and validate it before you move on."

The importance of asking probing questions

Coaching isn't a prescriptive process. It relies on effective questioning to understand a business owner's challenge, their options and the impact of those choices. Dr Brown says:

"Don't tell, ask. We're not in the telling game, we're in the asking and facilitation game. The key thing is to listen to what the client is saying and really probe.

"It's not just asking questions in chronological order. It's spending time understanding why something is an issue, why something is a goal today."

Questions have to be specific to the client, but Carlton provided a number of examples:

  • What would you like to change about the current practices or strategic approach?

  • What does a good outcome look like for you?

  • What options would you consider in dealing with this situation? What else would you consider?

The process helps Carlton uncover the underlying issue. For example, a business owner might be concerned about their sales team's performance but the problem is the resources the employees have. Dr Brown says:

"Once you ask the question, it's about drilling down. To get them to consider the implications. Ultimately, this is about decision making and making sure you're making better decisions."

Karen Eyre-White asks, "What's the one small thing that you could do to get there?" to help people become action-oriented and look at what's holding them back.

Challenging a business owner's thinking

Business owners often doubt themselves. Developing confidence and a growth mindset – a belief in continual improvement – can have a big impact on their chances of success. This means that challenging business owners' thinking is an important part of coaching.

Dr Brown says:

"I'm not afraid to challenge their thinking. That's really important. It's easy to go along to get along. That's not what it's about. None of us are the custodians of great ideas. It's about getting them to think of options."


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