Caught in the Middle

The Adviser’s Dilemma

A monthly column where Emma unpacks real-life situations from across the profession and shares a fresh perspective.
Each month you'll find the latest column published here and also featured in Money Marketing Magazine.
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Dear Emma,

We have a long-standing, high-value client who is warm and charismatic, and has become a personal friend. He has also recommended me to several other valuable clients.

The difficulty is that he can be dismissive, and at times rude, to my team. It is mostly subtle: ignoring our receptionist, making undermining comments to junior staff, that sort of thing. Nothing explosive but it is noticeable, and it adds up.

I don’t think he fully realises the impact of his behaviour. I tried to raise it once but he brushed it off with a joke. My team hasn’t complained directly, but I can tell it is affecting them. And, if I’m honest, I think it is starting to affect how they feel about me too.

The hard part is that I really like him. He has also been generous to the business and I don’t want to lose the relationship. But I also feel I’m not doing right by my team.

I’ve mostly avoided addressing it, hoping it would blow over; or perhaps hoping he would realise and change his behaviour. But that hasn’t happened and I’m starting to think I need to tackle it properly.

My team and my business are obviously more important than any one client, and I’d like to think I take my leadership responsibilities seriously. But I feel caught.

What should I do?

Yours,
Caught in the Middle

Dear Caught in the Middle,

What stands out most in your letter, reflected so clearly in your sign-off, is the feeling of being pulled in two directions. As if you’re standing alone, with your client on one side and your team on the other, and you’re being asked to choose between them.

On one hand, you could stand with your team and confront the issue with your important client and risk losing him. On the other, you could protect the client relationship and risk undermining the values and cohesion of your team.

That is a tough place to be, and I’m imagining it leaves you feeling burdened and alone.

In an attempt to support you, I want first to address your statement that you’ve mostly avoided addressing the situation, hoping it will blow over.

I want to offer a reminder that, of course, avoidance and silence still have a voice. Silence can communicate loudly. To your team, it might shout, ‘This isn’t mine to deal with.’ To your client, it may shout, ‘I’m not hearing you.’

Second, I want to reassure you that taking action doesn’t have to mean conflict or even choosing sides. In fact, it could open the door to a deeper connection and a stronger, more honest relationship on all fronts.

A helpful way into this might be to start with curiosity. Curiosity about your client’s experience, your team’s experience and your own. Often, the most impactful leadership doesn’t begin with answers but with questions and listening.

You might start a conversation with your client like this:

“I’ve been reflecting on how things are going across the team, and I wanted to check in on how you’re experiencing our service more broadly. Are there places where things aren’t working as well as they should be? I’d love to understand what’s happening from your perspective.”

This opens the space for dialogue, not defensiveness. For listening to understand, not to rebut or defend or minimise.

From there, if it feels right, you might say:

“In part, I ask because I’ve noticed moments where you’ve seemed frustrated, or perhaps a little dismissive with my team. I want to understand what might be behind that, because I care that you feel well supported, and also because the culture here really matters to me, and I want my team to feel valued and empowered to do their best work.”

Of course, it’s important that you find your own words. Find a way to express this sentiment in a way that feels natural and authentic to you. I encourage you to practise a couple of times first, with a peer, a friend or family member, or even in the mirror.

This is not about criticism. It’s about connection, curiosity and care (all the Cs). It establishes the conditions upon which trust can be laid and maintained, demonstrating benevolence, integrity, transparency and relational competence and courage. And it shows a style of leadership and service provision that is collaborative and co-created.

As well as speaking with your client, I encourage you to speak to your team with all the Cs above. Give them an opportunity to speak out about their thinking and their feelings. Resentment can flourish more easily in silence.

It might help you to use a visual image to support you. Instead of you being in the middle, with your client on one side and your team on the other, you might see yourself in a huddle. Not outside it as a referee. Or inside it as a target. But together, as part of the whole.

Because you are not standing alone on the outside, needing to choose a side here. Rather, you all stand together, each with a role in this relational dynamic.

You, of course, are very much part of this whole, faced with an opportunity to lead from within.

Warmly,
Emma

A CEO in conflict