The Uncertainty is the Worst Bit

Difficult Conversations Blog Header Image

There is a particular kind of silence that settles in workplaces when something important is not being said.

It shows up in meetings where people nod but do not quite agree.
In Teams messages that feel polite but tense.
In performance issues that are discussed everywhere except with the person involved.

We often describe these as “communication problems”. In reality, they are capability gaps.

The ability to navigate difficult conversations at work is not innate. It is learned. And in today’s evolving workplace, it is one of the most important professional skills we can develop.

Why Difficult Conversations Feel Harder Than They Used To

Work has changed.

Hybrid models have reshaped visibility and trust. Flexibility has raised new questions about fairness and contribution. Expectations around inclusion and belonging are rightly higher. At the same time, performance pressures have not eased.

In a recent newsletter, we explored how quickly narratives around productivity and flexibility can become polarised when left unchecked. We also highlighted how assumptions, particularly about commitment or contribution, can quietly influence how we interpret others’ behaviour.

These tensions rarely explode overnight. More often, they simmer.

And when we lack the language or confidence to address them constructively, we default to one of three responses:

Avoidance
Over-accommodation
Over-correction

None of these build trust.

What Actually Makes a Conversation “Difficult”?

A conversation becomes difficult when three elements are present:

High stakes – The outcome matters.
Strong emotion – There is frustration, fear, defensiveness or embarrassment involved.
Uncertainty – We do not know how the other person will respond.

This might relate to:

Giving developmental feedback
Addressing underperformance
Challenging biased language
Clarifying expectations in hybrid teams
Resetting boundaries
Discussing fairness or workload

The difficulty is rarely about the topic alone. It is about identity and impact.

We worry about being seen as unreasonable.
We fear damaging the relationship.
We do not want to appear unsupportive.
We are concerned about being misunderstood.

Understanding this psychological layer is the first step towards handling these moments well.

The Hidden Cost of Avoidance

Many professionals equate harmony with health. But surface harmony can conceal deeper dysfunction.

When concerns go unaddressed:

Assumptions harden into narratives
Resentment accumulates
Psychological safety diminishes
Small issues compound into significant conflict
Performance conversations become more intense than necessary

Avoidance often feels kind in the short term. In the longer term, it is rarely fair.

Clarity, when delivered respectfully, is an act of integrity.

Reframing Difficult Conversations as Developmental Conversations

One of the most powerful mindset shifts is this:

A difficult conversation is not something to “get through”.
It is an opportunity to create alignment.

When handled skilfully, these conversations can:

Strengthen mutual understanding
Clarify expectations
Surface hidden assumptions
Improve performance
Build trust rather than erode it

The key lies in moving from confrontation to curiosity.

Instead of asking, “How do I say this without upsetting them?”
We might ask, “How do I explore this in a way that increases clarity and shared ownership?”

That shift changes tone, posture and outcome.

Practical Principles for Respectful Dialogue

While every situation is unique, several core principles consistently improve the quality of difficult conversations at work.

Separate Facts from Interpretation

Before entering a conversation, pause and examine your assumptions.

What have you observed objectively?
What story are you telling yourself about it?

For example:

Fact: Deadlines have been missed twice.
Interpretation: They are disengaged.

Entering a conversation grounded in observable behaviour rather than personal judgement reduces defensiveness and increases credibility.

Clarify Your Intention

Are you seeking to:

Win an argument?
Prove a point?
Or improve a situation?

Being explicit with yourself about your purpose helps you regulate your tone and choose language more carefully.

Intentional conversations feel different. They are steadier, more focused and less reactive.

Regulate Before You Communicate

Strong emotion is not a sign you should avoid the conversation. It is a signal to prepare more thoughtfully.

This might involve:

Taking time before responding
Writing down key points
Practising neutral language
Anticipating potential reactions

Emotional regulation is not suppression. It is about ensuring your delivery aligns with your intention.

Use Language That Invites Dialogue

Certain phrases escalate quickly:

“You always…”
“You never…”
“Everyone thinks…”

These generalisations trigger defensiveness.

More constructive alternatives include:

“I’ve noticed…”
“Help me understand…”
“Can we explore…”
“My concern is…”

The goal is not to soften the issue beyond recognition. It is to create space for response rather than resistance.

Acknowledge the Wider Context

In conversations about flexibility, workload or fairness, context matters.

Hybrid working has changed visibility. Personal responsibilities differ. Perceptions of contribution can be influenced by unconscious bias.

Recognising this complexity does not dilute accountability. It strengthens it by ensuring expectations are explicit rather than implied.

Close with Clarity

Many difficult conversations fail not at the start, but at the end.

Without agreed next steps, alignment remains fragile.

Effective closure includes:

Clear expectations
Agreed actions
A shared understanding of what success looks like
A follow-up point

Clarity is respectful. Ambiguity is not.

The Link Between Difficult Conversations and Inclusive Cultures

Inclusive workplaces are not those without tension. They are those where tension can be expressed safely.

When people feel able to:

Challenge ideas
Raise concerns
Offer alternative perspectives
Receive feedback without humiliation

…innovation and trust increase.

Avoiding difficult conversations in the name of inclusion can have the opposite effect. It protects comfort rather than fairness.

Respectful dialogue, even when uncomfortable, is foundational to cultures built on transparency and integrity.

Communication as a Strategic Skill

Too often, communication is categorised as a “soft skill”. Yet the ability to navigate difficult conversations influences:

Retention
Engagement
Performance
Team cohesion
Reputation
Leadership credibility

In complex, flexible and diverse workplaces, this capability is not optional. It is strategic.

Professionals who can combine empathy with accountability, curiosity with clarity and courage with composure are better equipped to lead and collaborate effectively.

Continuing the Conversation

At WorkJuggle, we believe that education empowers better work. Our new programme, Difficult Conversations Made Easier was designed to build exactly these capabilities through practical, scenario-based learning.

If you are looking to strengthen your own approach or support your team in navigating challenging conversations with greater confidence and integrity, we invite you to explore the programme in more detail.

Respectful dialogue is not about avoiding discomfort.
It is about using it constructively.

And that is a skill worth developing.

Learn more about our Difficult Conversations Made Easier 1 day virtual programme here.

Feb 3rd ’23

I was speaking to a few people this week who are waiting. Waiting on news, waiting to hear about possible jobs losses. The headlines are slowly becoming reality as LinkedIn lights up with tales of people getting emails in the middle of the night telling them their job is gone. When I was speaking with those people the one thing I echoed again and again is “This is the worst bit. The uncertainty is always the worst”.
In my experience that is true, it is is the not knowing which is a killer. It is not being able to plan, wondering who is next and if that person could be you. I have had two personal experiences of job loss. The first was well flagged, a voluntary redundancy package which I had eagerly stalked for over a year. It was a substantial sum of money and I was drowning trying to manage a job with no flexibility and two small children. The day I got the news my name was finally on the list I opened up a bottle of champagne and started the plans to build a new house. The package gave me financial stability and the freedom to stay at home for a few years. It was a great day.
The second time I was impacted by job loss it was most definitely not a great day. The news came in on Christmas Eve. It was not expected and by then we had three still quite small children, substantial outgoings and I was not working. It sent me into a tailspin of sleepless nights, spreadsheets and budget planning (Hello MrMoneyMoustache & Caitriona Redmond, you are still my heroes!). It became impossible to plan for the future and it was an incredibly stressful time.
I imagine for most people who are being made redundant they will fall somewhere between those two extremes. There will no doubt be people who had become tired of corporate life and had other aspirations but for most people I imagine it will be unplanned and difficult.
Having been there (twice!) my advise is this.. Plan for the absolute worst. I appreciate this may seem counterintuitive and runs contrary to the toxic positivity mindset we have all been inculcated with. However in my experience planning for the absolute worst is actually really helpful. The key is to write it all down. Think about what is the worst that could happen (losing your house is always top of my mind) and then work out what that would look like. Once you have your health it is often not as bad as you may think. From there work out a financial plan. If you are worried about money it becomes very difficult to think creatively about what your future may look like. Once you have a plan I think it becomes a little easier to look forward.
Finally as I mentioned in my first newsletter, LinkedIn is very definitely not your friend. Not now. There is nothing to be gained from hearing other peoples stories. Later when you are looking for a job LinkedIn is great but right now head space and clarity of thought are vital and social media never provides much in the way of either of those two.
There are always fresh starts. We are hiring for tech jobs at the moment the need for people to work in Technology has 100% not gone away, you can take a look at them here. We are also delivering a programme for Women Returners on the 13th of March which you apply for here. To new beginnings.
Till next week,
Ciara
What we are Reading
I read this article in the NYT about a best selling author, Elin Hildrebrand whom I had never heard of who hosted a hugely popular weekend in Nantucket where many of her books are based. I was intrigued and bought her book “The Hotel Nantucket”. It is a hugely comforting beach read and just the thing for these still dark nights. The sunshine practically bounces off the page.
Listening To
Big fan of Claer Barret’s, The Money Clinic. Although UK based it is always interesting. She sounds just like what you might imagine the head girl in Mallory Towers would sound like, which I find oddly comforting.
What we are Watching
Somebody Somewhere Set in Kansas, the NY comedian Bridget Everett imagines her life if she had never left her home town. It is funny, sweet and believable.