When and How to Share Tough People Decisions Before the Holidays
When and How to Share Tough People Decisions Before the Holidays
obijames
As the year draws to a close, I’ve been spending a lot of time thinking about a question many leaders quietly wrestle with:
When and how should we share tough people decisions before the holidays?
After sharing a post about this recently, I heard from many of you – in comments and private messages alike. Leaders, HR partners, and people who’ve been on both sides of these moments.
What struck me most wasn’t agreement, but how common and heavy this dilemma is.
So for the benefit of others who might be carrying similar worries, here are a few reflections I’m taking with me as the year wraps up.
What feels clearer after listening:
A few themes came through consistently:
- There is no universally “right” time. Different people genuinely prefer different things, and the same timing can land very differently.
- Waiting doesn’t remove harm; it often moves it into uncertainty, which many people find harder to hold than truth.
- Early clarity can give people agency – time to process, reflect, and begin orienting toward what comes next.
- Context is everything, and timing alone isn’t the point. How news is shared – with dignity, care, and support – matters just as much as what and when.
- Survivor guilt is real and often overlooked. Those who remain are impacted too, and that deserves attention.
- As inclusive leaders, we must remember that there is no way to avoid every holiday or meaningful moment.
- Ultimately, compassionate delivery and follow-up matter more than trying to find the “perfect” moment.
Where I’ve landed (for now)
I’m still not certain, and certainty was never the goal here.
What I remain very clear about is this:
- silence has a cost
- ambiguity has a cost
- and those costs are most often carried by people with the least power
What helps most isn’t perfection, but transparency and careful courage – being willing to make hard calls with as much humanity as possible, and not leaving people alone with their imaginations whih can fuel anxiety.
If you’re holding a decision like this as the year closes, you’re not weak or unkind for finding it heavy.
You’re human.
Thank you to everyone who shared so openly and thoughtfully. You made this feel far less lonely and I am grateful.
About Obi:
Obi James is Director of Obi James Consultancy, partnering with organisations, HR, and OD leaders to strengthen the relational and systemic conditions that support trust, clarity, and effective leadership.
A Team and Leader Coach, and author of Let Go Leadership, Obi designs and delivers Senior Leadership Team Accelerator programmes, Leader-as-Coach development, and a 12-month Leadership Catalyst Programme for mid-level and succession-ready leaders to build sustainable leadership capability, confidence, and organisational resilience.
