There really is just something about December that makes us question our career at one point or another. November is generally when you start to see the breadcrumb signs that someone is considering a move. Think less LinkedIn profile updates and more subtle signs of end-of-year fatigue manifesting as withdrawal.
If you’re responsible for a leadership team, the prospect of an unexpected resignation come January is probably already on your radar and if it’s not, it should be. Once year-end bonuses are paid and with the pressures of work behind them for a few short weeks, December gives senior leaders something they lack during the year: real space and time to ask themselves whether they have another 12 months in them.
At this point in the year, when you’re finalising budgets, workforce plans and year-end reports, you might already suspect which senior team members are a flight risk. If you can relate, you’ve got roughly seven weeks before your leadership team heads on break, which gives you ample time to have some honest conversations.
While resignation signals are not made overnight, there are often subtle signs and shifts in behaviour worth paying attention to. None of these are of course definitive in any way, but a noticeable change in how a leader engages, contributes or talks about the future can be worth a closer look.
Here are some common signals to pay attention to as we head into the final weeks of the year.
Losing interest in key planning.
You’re in the depths of workforce and budget planning for 2027 and well, they’ve just gone quiet. Where previously they’d be motivating for certain outcomes and fighting tooth and nail for people and budget, they just ‘go with it’. This shift in behaviour may be a sign they’re no longer as invested in the future of the business they’re being asked to shape.
Stops challenging decisions.
Usually you can count on them to play ‘Devil’s advocate’ when it comes to problem-solving and especially hiring. It’s a good sign of investment and passion in what they’re doing, which is why when a strong leader who historically challenges decisions suddenly stops, it may warrant a conversation to explore why.
Significant organisational change.
Everyone is trying their best to keep pace with how fast our world is changing, sure some are better at adapting than others, but what if the change alters your experience or expectation of what attracted you to the company or role in the first place? Organisational change can invite leaders to question whether the business (and their place in it) still aligns with where they are currently and where they want to go.
Completing a milestone.
It’s not uncommon that senior leaders view their careers in milestones or chapters. Completing a major transformation, delivering a long-term project or reaching a career milestone can naturally encourage a leader to ask themselves what’s next?
Losing valuable people.
Probably the hardest and most obvious signal can be the impact of losing great people, this one always hurts. Team departures often reveal unspoken context about leadership confidence, team stability and even insight into the external market.
No one would willingly want to start a new year with resignations from core executives, particularly if they’re a leader who has significant impact when it comes to productivity, culture or strategy.
When or if you suspect an executive flight risk, proactively set up a session to get ahead of it. Use the time as an opportunity to ask considered questions that make them feel seen and heard but also to understand what’s driving any uncertainty and whether there’s anything truly meaningful the business can do or change.
I’ve included some helpful questions that I’ve used in the past to drive some of these leadership conversations. It’s worth noting that the last question can be an uncomfortable one, what I’ve learned over time is that those who answer honestly are telling you exactly what to fix, and when someone struggles to answer, that can be a useful sign to explore what might be going unsaid. The three questions:
- What’s frustrating you that people might not be seeing?
- What would make next year your best year here?
- If someone called you about a potential job opportunity, what would make you take the call?
By the time a resignation lands, the conversation often shifts away from understanding what’s wrong to convincing them to stay and usually coupled with a last-minute counter-offer made under pressure. The sad truth is that too many businesses only discover what a senior leader was thinking during an exit interview and even then, they don’t always uncover the underlying reason(s) someone has truly decided to leave.
Start by planning the tough conversations
The gut never lies, so once you have an inkling that a leader is a flight risk, begin by understanding the basics before you head into a conversation. From how the resignation will impact the direct team, clients and business to important specifics about their notice period and handover requirements.
Yes, some of these conversations will go well, but we’d always recommend planning for the ones that won’t, first.
Here are some useful questions to answer before you send off that meeting request, so you’re not caught off guard should that resignation you had a feeling about hit your inbox:
For each senior leader you suspect might be a flight risk, understand the following:
Questions to clarify ahead of setting up the meeting:
Interim cover
Sometimes an immediate replacement is not always possible and interim cover needs to be considered.
Use this time to craft an interim cover scenario plan.
- Could the cover come from inside the business or would fractional support be a better approach?
- What are the critical role requirements, responsibilities and ownership areas that need to be covered for the first 90 days to reduce wider team and business disruption?
- What are the potential knock-on effects should interim cover come from inside the business?
Internal successor
Start with understanding if there is a succession plan in place or if one needs to be created. Clearly map out:
- Who could step up?
- What is their level of readiness?
- What do they require to be successful?
- How will their shift in role impact their current work and team?
- Will this step up require a permanent replacement hire or could bringing in a contractor to support the shift be a better solution?
- How will their title, job description and salary requirements need to be adjusted?
Exit terms
Where there is a flight risk concern, use this time to revisit their employment contracts, get clear on their notice period, restraint of trade and handover obligations.
The external market
Sometimes hiring internally isn’t an option, so use this time to get a better understanding of the external market.
Engage a recruitment advisor or executive search firm to help with market mapping, salary benchmarks, talent availability, notice periods and the viability of permanent versus contract placements. This will give you a clearer picture of the landscape and what’s realistic.
Doing this groundwork ahead of time puts you on the front foot when it comes to resignation season. It’s also worth knowing that in today’s market, many exceptional leaders aren’t actively looking for their next role, so identifying, approaching and appointing those leaders takes time. It’s time you may not have if your search only begins after an unexpected January resignation.
Use December to get ahead of January
You may well start the new year with your leadership team intact, if you do, the work still pays off. You’ll go into 2027 knowing your bench, your risks and your options, and be better prepared for the questions your board may ask about leadership continuity. If someone does resign, you’ll have a validated contingency plan in hand and a job spec ready to push live.
Acuity has spent 17+ years helping businesses appoint leaders they can’t afford to get wrong.
Our executive search process starts with understanding the hiring and business challenge you’re trying to solve, defining what success looks like beyond the job description and mapping the leadership talent available in the market, including those who aren’t actively looking.
If there is a critical seat on your leadership team you’d struggle to fill at short notice, let’s have a confidential conversation before the year closes.