Strategy is About Choices
Strategy is the process of identifying choices of action, weighing the outcomes and risks of those actions, and then making a clear choice. Hope is not a valid strategy, especially when it comes to retaining your employees. For a solid employee retention strategy to be effective, you must understand the reality, and involve your management staff.
Get Real About What Retention Means
Strategic question: What’s more critical, retaining the employees themselves, or retaining your team’s ability to achieve results? Getting real about this question can surface some real trade-offs and costs. Is recruiting a challenge for your org, or do you have a plentiful talent pool you can access quickly? Are your roles difficult or easy to backfill?
Understanding “what” you’re trying to retain is important to shape your next strategic choices.

The “Better by…” Circled Date
Unless an employee is 100% smitten with your company they have a date circled on a calendar (either in their head, discussed with their spouse, or literally on a calendar). How heavy the circle is depends on a lot of factors, but everyone has one.
If things don’t get better by this date I’m going to start thinking of making a change.
Some factors that influence the Circled Date:
- The promotion cycle. Even if they got promoted, or if they’ve gotten passed up, you can bet that it is a convenient time to leave after the promotion cycle resolves.
- The day they get their bonuses/401k vesting payout.
- Expected org changes, M&A
- Bored, unfulfilled, not challenged.
- Burned out due to “busy” crunchtime periods.
- Personal conflicts with other coworkers.
But which factor is causing it? Depending on where you sit in the organization, your best information is something like an employee satisfaction survey. While that’s a solid resource to rely on, it may not reveal the full picture.
It Starts at the Interview
I’ve interviewed a thousand+ candidates. Candidates are amazing data points of retention failure of their current companies (except for new grads, obviously).
I’m sure you’ve heard this sentiment: “You don’t quit your job, you quit your boss”. The reality is not quite so clean and tidy as that pithy saying might indicate. The statement should be more like “People don’t quit their job, they quit over their manager disappointing them by not meeting their expectations.”
My all-time favorite interview questions I ask (and I hope you steal it) is:
This may sound a bit odd, and please don’t identify them specifically, but… Who was the worst manager you’ve had and why?"
Follow-up: ‘What about the best?’
I love this question because it unlocks many layers of exploration about what a person is looking for in their manager. Half the time, without asking directly, the candidate offers a clear picture of why they left their previous job. If you interview enough candidates you notice that responses fall into a couple buckets.
Answer: “I wasn’t growing”
Reality: There are limits or thresholds that exist way outside the control of any manager. But, the manager needs to be the responsible voice of the organization and toe a line of not throwing the whole of the organization under the bus. The org expects the manager to enforce the policies and own the delivery of the news. Is that often unfair to the manager? Yup. No one said this job is easy.
Strategic Considerations: Consider how managers are maintaining career progression expectations throughout the year and how often goals are being discussed with the direct. Actively seek out issues of avoidance of “tough conversations”. If you intuit that a manager isn’t managing the performance expectations of a direct appropriately, follow-up with the manager to determine if they’re softballing their direct. Ask for notes and follow-ups. The earlier the better.
Answer: “It was just time” aka Comp Cycles
Are promotion and compensation at your organization tightly coupled and cyclical? That might be subverting the retention opportunities your comp program provides.
Promotion is usually conflated with raises and bonuses. This ties a critical monetary moment to a calendar date that signals to the direct that it’s a “good time to leave” after that delivery. Especially if they have to wait a whole year to get another stab at it.
A more consistently repeating (even if lower total comp) compensation cycle can produce a regular feeling of financial reward positive feedback loop. For example, consider “award” or “spot-bonus” compensations quarterly or monthly, to keep folks engaged and not circling a date in their calendar when it’s a good time to quit.
Answer: “My current boss is the best”
A highlight moment in the interview process (besides offering) is when they answer that their best boss is their current one, because I get to ask: “If they’re your favorite boss, why are you leaving?”. It provides so much insight into what they value and what they’re looking to get out of a job.
It is true that there are verifiable “bad” managers. It’s awful to be on the receiving end of an abusive, controlling boss. Been there. In my experience the likelier reason for exits is due to the factors they view the manager as should be able to control, but aren’t.
Your Managers Retain Employees
Your management staff needs to be at the core of your strategy. You rely on them for weekly touchpoints with their directs, and therefore understand the pulse of your staff. If you ask, you can rely on them for a 2-3 bullet list of what could help them retain employees.
Don’t be surprised if their asks include a mix of start-doing and stop-doing. Be understanding, upfront, and clear about options available to respond to concerns. You won’t be able to address all concerns, but it’s crucial to have a consistent and clear understanding of the problems your managers are hearing.
Summary
If you are investing in improving your employee retention strategy, make sure you have:
- Information about why each of your employees left their previous job
- Actionable and regular boots-on-the-ground feedback from your management staff
- A compensation schedule that doesn’t cause Circled Dates, e.g., a great day to quit.
Otherwise, you’re missing out on a reliable predictor of retention causes.
