Difficult Employee Conversations: From Preparation to a Clear Next Step

Choosing the right support in Finland

If you are wondering how to prepare for a difficult conversation with an employee, start by identifying the kind of help you need. A conversation about missed deadlines is different from a formal disciplinary matter, a harassment allegation or a possible dismissal.

For leaders buying coaching or a self-guided resource in Finland, look for practical relevance rather than promises of a perfect conversation. Useful questions include:

• Does this support address your immediate situation and level of responsibility?
• Are the scope, price, format and confidentiality arrangements clear?
• Can you work in a language in which you can express sensitive points accurately?
• Does the provider distinguish leadership coaching from HR and legal advice?

For formal employment matters, check your organisation’s procedures, applicable Finnish employment requirements and any relevant collective agreement with qualified HR or legal support. Coaching can help you prepare your approach; it does not replace those checks.

For an everyday feedback conversation, you can begin with the preparation below.

Define the issue without judging the person

Write down the purpose of the meeting in one sentence: “We need to understand why the last two handovers were late and agree how future deadlines will be met.”

Then separate three things:

• Observation: What happened, and when?
• Impact: What effect did it have on the work or other people?
• Interpretation: What are you assuming about the reasons?

“The report arrived on Thursday rather than Tuesday” is an observation. “You do not care about the team” is an interpretation. Bring the first into the conversation and be prepared to question the second.

Check whether the expectation was explicit, realistic and within the employee’s control. Your preparation should include your own contribution: unclear priorities, conflicting instructions or delayed decisions may be relevant.

Decide what is fixed and what is open

Clarify what you need to communicate and what you still need to learn. You may need a required standard to be met while remaining open to how the employee achieves it.

Prepare a small number of questions:

• “How do you see what happened?”
• “What got in the way?”
• “Were the priorities and expectations clear?”
• “What support or change would help?”

Do not present a decision as a consultation if it has already been made. Equally, avoid deciding the explanation before you have heard the employee’s account. Fairness requires genuine room for information that could change your view.

Arrange a meeting that allows a proper discussion

Choose a private setting and allow enough time that neither person has to rush straight into another commitment. Give an honest indication of the subject, rather than a vague invitation that leaves the employee guessing.

For example: “I’d like to discuss the recent project handovers, understand what has been happening and agree expectations for the next delivery.”

If the matter is formal, use the appropriate process for notification, attendance and any representation or support arrangements. Do not disguise a disciplinary meeting as an informal catch-up.

Before the meeting, notice your emotional state. If you feel angry, rehearse the facts aloud and remove language intended to punish, shame or win an argument.

Prepare your opening, not a complete script

A useful opening names the issue, explains its significance and invites a response:

“Two recent handovers arrived after the agreed deadline. That left the delivery team less time for review. I want to understand what happened and agree how we handle the next handover. How do you see it?”

Then stop and listen. Avoid stacking several unrelated complaints into the opening.

If the employee disagrees, ask which facts or expectations they see differently. If new information emerges, investigate rather than forcing an immediate conclusion. If emotions rise, acknowledge the difficulty and consider a short pause. You can remain respectful without abandoning the issue.

Plan how you will close and follow up

Aim to leave with clarity about the next action, who owns it, what support is available and when progress will be reviewed. Where appropriate, agree what successful improvement will look like.

Summarise the discussion and invite corrections. Record relevant facts and agreed actions proportionately, following your organisation’s privacy and record-keeping policies. Distinguish between what was agreed and what remains disputed.

Who Jessica Hill Holm is and why her focus is relevant

Jessica Hill Holm, of Hill Holm Leadership, is an Executive Coach & Advisor whose work focuses on building and transforming innovation-driven companies alongside CEOs and founders, with a People & Culture focus.

That positioning is relevant when an employee conversation is also a leadership challenge: balancing accountability, relationships and organisational needs. You can review her professional profile on LinkedIn when considering fit.

Take the next step

If you want to work on this yourself right now, explore Jessica’s workbook, The Difficult Conversations Playbook, as a self-guided starting point.

Leaders facing difficult conversations at executive level can book a free discovery call to discuss their situation and whether Jessica’s support is a fit.