Critical conversations for business success …and six ways to make the most of them

Apr 18th, 2023

Critical conversations for business success …and six ways to make the most of them


Many business leaders tell me that the most challenging part of their role is not driving their business forward, but the managing of people. Specifically, the need to dedicate time to the critical conversations that ensure their teams are motivated and allow them to predict and address any potential issues that may arise.

It is easy for the more ‘commercial’ aspects of a business leader’s role involving clients, board discussions, etc, to be prioritised. However, investing the time into having meaningful engagement with your teams can have a huge commercial impact if ignored. As with anything in life that is important, you need to commit time to it.

In my experience there are key critical conversations that business leaders need to be having regularly that will always matter and, in the end, make their lives easier.

Here I look at six important conversations with teams and clients that can make a difference to a leader’s success in business….

1. Begin well – the foundation meeting

For every new business relationship, it is important that they begin well. Whether with a new member of staff or a new client, the initial foundation meeting is a chance to find common ground and values, ask important questions and set out the ground rules and expectations for how the relationship will work and what it will need to succeed.

I view the foundation meetings that I have with clients as critical and would not begin my work without them. They enable me to build trust, get to know their values and drivers, clarify their ambitions and be clear on what success looks like for them so we are both clear.

Often when I hear leaders express frustration about team members not performing or undertaking tasks in the way they would like, I will ask them if they have ever explicitly set out what they expect from them. Commonly when they reflect on this, the answer is ‘no’.

This can lead to a lack of understanding about the culture and behaviours within the team that are critical to success, and the boundaries and behaviours that could impact this.  Assumptions are made in the absence of this which can create setbacks.

A client who relocated from the USA recently told me about his approach when preparing for the induction meeting he holds with new starters, which I really liked. He has created what he refers to as his ‘user manual’, which is sent to his teams to help new team members understand him and how he works. I was impressed when I read it as he explains what he likes, what he wants, what he values, what annoys him, his ‘annoying habits’, and how he likes to communicate. This document is filled with his personality and values. It makes it easier for team members to get to know him and have a valuable insight into their new boss.


2. One-to-Ones that are more than reviews

Having observed many one-to-one meetings over the years, many of them do not always have a clearly defined purpose – it can vary from a work in progress review or dedicated time to have a more personal chat about how people are getting on.

Most leaders appreciate that in addition to annual reviews, it’s critical to schedule regular time individually with each of your team members.  When managed well it is a meeting that your colleagues value, and know they will leave feeling motivated, clear about their development and what will be key to their ongoing success and the success of the business.  I propose leaders speak 30% of the time during this meeting so their ability to ask good questions and listen is important.

Many of us have felt the impact of a key member of a team resigning. When leaders express surprise when this happens I always question their commitment to one-to-ones. If managed well they will reveal the early signs of discontent, unmet ambition or a lack of motivation. This gives leaders the opportunity to address these before the decision to leave is made and its full impact is felt – from a commercial and a team morale perspective.


3. Use your Business Plan as an active tool

Business plans take a long time to write, but too often are then left in a drawer, only to be reviewed once or twice a year. Instead, make your business plan your strategy compass and use it as a point of reference in team conversations.

Summarise your business plan into your vision and the key goals.  Use time in monthly meetings to review one specific goal or objective.  Encourage open conversation around progress that has been made, what has been achieved and what is outstanding and why.  If market conditions change there may need to be agility in how you pivot according to those changes and this regular strategic discussion will ensure you are thinking ahead and prepared for this.


4. Tackling Conflict

Many people will acknowledge they have a tendency to avoid conflict in order to maintain positive working relationships, but controlled, constructive conflict can strengthen relationships and establish opportunities for business growth.

I recall working with two co-founders who had been friends for many years. Their relationship had become strained and they were no longer speaking to each other in a constructive way. This tension had been picked up by their team and was demotivating staff. Without resolving the co-founders relationship, it was clear that the business was going to suffer.

We took one of our meetings away from the office and went for a walk in a local park. The dynamic of walking with both founders on either side enabled each of them to look ahead and answer questions such as ‘What do you appreciate about each otherWhat is your biggest challenge right now? without having to look at each other across a table.  It allowed one of the directors to express his frustration that he was no longer enjoying the work he was doing because his remit had changed. It was the first time that this had been voiced, and led to a more constructive conversation about being able to find a solution.  As a result their roles were redefined leveraging their strengths which their teams and the business benefited from.


5. Motivational team meetings

Having a ‘meetings culture’ is often a pain point for teams and management. It is therefore important to regularly review your approach to meetings. Are they motivating your team? How valuable and productive are they? Are the right people in them? Are core meetings prioritised?

A client I have worked with for a number of years has assigned one day a week where no meetings are booked in order to allow at least one day for focussing on tasks – as back-to-back meetings online and in-person had resulted in no time to execute.  When talking to her recently she reported that this has improved productivity.

Another company has introduced the policy that all internal meetings are held between 10am and 4pm so that working parents don’t have to make a decision between attending a meeting and doing the school run.

Every 6 months it is helpful to do a review with your teams by asking:

  • From 0 – 10 how valuable is our weekly team meeting?
  • What do you want to continue?
  • What do you want to stop/change?
  • What do you want to start?

In this way they take ownership of meetings that would add value to them where everyone benefits.


6. Understanding your clients’ needs now and in the future

How often do you have deeper conversations with your clients outside of the regularly scheduled update meetings?

Whilst regular tactical meetings with the wider delivery team are an important part of staying on top of the service being delivered, they often don’t allow for wider strategy discussions.

How much do you know about the future trends in your clients business, their current biggest challenges, what aspects of your service they particularly value, and where they feel you could add greater value?

Diarising bi-annual top-level discussions provides a forum for critical conversations that might not be able to happen in front of wider team members. Having a space where wider strategy and sensitive topics can be openly discussed opens up a platform for giving advice that may challenge the client and challenge you.

One of my favourite books is The Trusted Advisor by David Maister and it explains the key characteristics of the Trusted Advisor (a term I hear many companies talk of).  Some of them include:

  1. ‘Showing  a strong competitive drive aimed not at competitors, but at constantly finding new ways to be of greater service to the client’
  2. ‘Seeking out (rather than avoiding) client-contact experiences and taking personal risks with clients rather than avoiding them’
  3. ‘Acknowledging the reward of a trusted advisor relationship, for both client and advisor, is that individuals are most able to be fully who they are and energy is not expended protecting themselves. Both can be open with information about their lives, their strengths and their weaknesses. They share information and ideas, feel comfortable with themselves and have great access to their emotions and inspirations’.

These characteristics can apply to all aspects of a successful business relationship.

Whether it is with clients or colleagues, businesses will benefit from having leaders who make time and create habits for having these important conversations so they, and all they serve, can flourish.


If you would like to talk more about the critical conversations that will make a difference to you and your business please contact me at