Having Effective Difficult Conversations at Work

Every finance professional who manages people eventually has to deliver news someone doesn't want to hear — a missed promotion, a performance concern, a budget cut that affects someone's role, or feedback about behaviour that's damaging a team. Avoiding these conversations, or handling them badly, doesn't make the underlying issue go away; it usually makes it worse, and slower to fix.

Why Difficult Conversations Get Avoided

Most people avoid difficult conversations because they conflate being direct with being unkind, or because a vague, softened version feels safer in the moment even though it's rarely kinder in outcome. A manager who hints at a performance problem rather than stating it clearly isn't protecting the other person — they're denying them the clear information needed to actually address it, while still leaving both people uncomfortable.

A Practical Framework for Difficult Conversations

1. Get clear on the actual message before the conversation starts. If you can't state the core point in one plain sentence beforehand, the conversation itself will likely be unclear too.
2. Lead with the substance, not a long preamble. A lengthy build-up usually signals discomfort to the other person before you've said anything, and makes the eventual message land harder, not softer.
3. Separate the behaviour or issue from the person. Describing specific, observable behaviour and its impact is both more accurate and less likely to trigger defensiveness than broader character judgements.
4. Make space for a genuine response. A difficult conversation that's really a monologue misses the chance to understand context you might not have, and rarely produces real buy-in.

Worked Example: Addressing a Missed Deadline Pattern

A finance manager notices that one team member has missed several reporting deadlines over two months, each with a plausible individual explanation. Rather than letting it continue unaddressed or escalating straight to a formal process, she raises it directly and specifically: naming the pattern (not just the latest instance), describing its impact on downstream reporting, and asking directly what's driving it before assuming the cause. The conversation surfaces a genuine capacity issue that hadn't been flagged, which is addressed through a workload adjustment — a far better outcome than either continued silent frustration or an adversarial escalation, and one only possible because the conversation happened at all.

Common Pitfalls

The most common mistake is over-softening the message to the point where the actual point gets lost — the other person leaves the conversation without a clear understanding of what needs to change. The second is avoiding the conversation altogether until the issue has escalated to the point where a much harder conversation becomes unavoidable, trading a manageable moment now for a larger one later.

Building This Into Team Practice

Managers who handle this well treat difficult conversations as a routine part of managing, addressed promptly and calmly as issues arise, rather than as rare, dreaded events saved up until they can no longer be avoided.

Why This Belongs in a Structured CPD Programme

People management and communication skills, including handling difficult conversations, are increasingly recognised as core professional competencies in accounting and finance qualifications, not just "soft" extras, and structured CPD gives them the same deliberate development as technical skills.

How This Fits Into a Broader Compliance Programme

Well-handled difficult conversations, properly documented, are also a governance safeguard — performance and conduct issues addressed early and clearly are far less likely to develop into the kind of unresolved, undocumented problems that create real legal and reputational exposure later.

Difficult Conversations Over Video or Chat

Remote and hybrid working means many difficult conversations now happen over video call rather than in person, and some managers default to email or chat instead because it feels easier — but written channels strip out tone and invite misreading, and are a poor substitute for a real-time conversation on anything sensitive. Where possible, difficult conversations should still happen live, by video if not in person, with a brief written follow-up afterward to confirm what was discussed and agreed. Reserving email for scheduling the conversation, not having it, keeps the actual exchange human and reduces the risk of a message landing far more harshly than intended.

FAQ

Is being direct in a difficult conversation the same as being harsh?
No — directness is about clarity of message, not tone. A conversation can be both clear and respectful; the two aren't in tension.

Should difficult conversations always be documented afterward?
For anything performance or conduct-related, a brief written record of what was discussed and agreed is good practice, both for fairness and for tracking whether things improve.

What if the other person becomes defensive or upset?
Staying calm, sticking to specific observed facts rather than broader judgements, and giving them room to respond usually helps de-escalate this more effectively than backing away from the message.

For related reading, see our guides to leadership essentials for new finance managers and conflict resolution and communication in the finance workplace. Build your team's management skills further with Learnsignal's CPD courses.