goals — BLOG — Next Levels Coaching

One of the most delicate leadership challenges executives face is managing employees nearing retirement. Unlike early-career professionals eager to grow or mid-career leaders striving for advancement, soon-to-retire employees may be in a very different mindset — one that prioritizes stability, familiarity, and winding down over growth, innovation, and risk-taking.

This stage can provide substantial value, as these employees often possess decades of institutional knowledge, strong relationships, and a long history with the company. But it can also present challenges when motivation, adaptability, or team alignment begin to wane. Organizational psychologist Daniel Levinson once described career life stages as “seasons,” each with its own developmental tasks. For leaders, navigating the “retirement season” with both respect and strategic foresight is critical for team health and company continuity.

Common Challenges of Managing Soon-to-Retire Employees

1. Declining Engagement. Some employees begin to mentally “check out” once they know retirement is near. They may resist learning new skills, avoid stretch assignments, or simply do the bare minimum. This can frustrate colleagues who feel they are carrying a disproportionate share of the workload.

2. Fixed Mindsets and Outdated Approaches. After decades of doing things a certain way, some employees may resist change. Carol Dweck’s work on growth vs. fixed mindsets underscores how damaging this can be to team progress. When a veteran leader refuses to adapt, it not only stalls innovation but can also discourage younger employees who crave guidance and support.

3. Negative Energy on Teams. Sometimes, the frustration of being “almost out the door” manifests as cynicism or dismissiveness. A skeptical, resistant attitude can undermine morale and stifle creativity, especially when an employee feels untouchable due to tenure or loyalty.

Organizational Dilemmas

1. Loyalty and Legacy. Long-serving employees often hold a special place in the organization’s story. Leaders may hesitate to confront underperformance because of past contributions or out of respect for years of service.

2. Team Morale. Even if performance has declined, many soon-to-retire employees are well regarded. Handling their transition poorly can harm morale and signal to others that the company does not value its employees.

3. Institutional Knowledge. In some cases, retirees hold critical knowledge that has not been documented or shared. This creates a “single point of failure” for the organization. Harvard Business Review notes that knowledge transfer during retirements is one of the most overlooked succession risks companies face.

Leadership Strategies to Manage This Transition

1. Set Clear Expectations and Address Performance. Respect does not mean avoidance. Leaders should continue to set expectations and hold soon-to-retire employees accountable. Frame it as ensuring that the legacy of their work endures within the team. Choose your battles wisely, focusing on issues that impact culture, client outcomes, or team cohesion

2. Redefine Their Role for Maximum Value. If motivation for new projects has waned, consider narrowing their scope to focus on what they do best. Moving them from management into an individual contributor or mentor role can enable them to add value without adversely affecting others. Taking time to understand their motivations at this stage can help you approach them more effectively.

3. Leverage Knowledge Transfer. Position them as mentors or “knowledge stewards.” Encourage them to document processes, coach rising leaders, or conduct training sessions. This not only preserves institutional wisdom but also allows them to leave a legacy.

4. Explore Internal Transitions. Sometimes, moving the person to a team or function that better aligns with their strengths can be beneficial. A lower-visibility role may help them finish their career with dignity while minimizing team disruption.

5. Plan for Graceful Exits. If performance issues outweigh contributions, it may be time to guide them toward a positive exit. Providing a strong retirement package and celebrating their contributions can soften the transition and signal that the company honors its people.

6. Build for the Long Term. Succession planning is the real antidote. Ensure no single person holds irreplaceable knowledge or critical relationships. Developing future leaders and creating systems for knowledge capture protects both the company and the individual.

Managing employees nearing retirement requires leaders to balance respect with accountability, empathy with decisiveness, and legacy with progress. When approached thoughtfully, these transitions can preserve institutional knowledge, strengthen culture, and honor contributions while ensuring the organization is prepared for the future.

Quote of the Day: “What you leave behind is not what is engraved in stone monuments, but what is woven into the lives of others.” -Attributed to Pericles, Athenian Statesman

Reflection Question: How has your organization successfully navigated the retirement of key employees? What strategies worked best to balance respect, performance, and continuity? Comment and share below; we’d love to hear from you!

The next blog in this series 5/7 will focus on another leadership challenge – leading dotted line employees.

As a leadership development and executive coach, I work with leaders to sharpen their leadership skills and navigate tricky situations like these. Contact me to explore this topic further.

The previous blogs in this series have covered various topics relating to how habits work and how we can make them work better. This blog will offer several tips to further optimize your habit changes.

1. Have Systems, not Goals. Scott Adams, in his book “How to Fail at Almost Everything and Still Win Big,” says when you are trying to make changes, it is better to have systems versus goals. He states how goals can be vague, such as I want to lose 10 pounds, but systems - what you will eat, how you will exercise, what research you will put into your plan, how consistent you will be - will determine the results you want. Sports coaches understand this distinction, you may have the goal of winning a championship, but it is a system of how you recruit players, run practices, and manage assistant coaches to get you to that result. Goals are about one moment, such as cleaning my house, but that’s temporary if you do not have a system in place of immediately putting things where they belong. It is essential to have both –set a goal so you know the direction you are going in and build the system to support your journey.

2. Get a partner. Sometimes when we are thinking of making changes, it can be easy to talk about it but hard to live. We are all human with weaknesses and willpower lapses and cannot always do it alone. Enlisting help, whether a supportive partner or a coach, can help us make sustainable changes. It is the reason why many people work with personal trainers. If all we needed were more information on diet and exercise, we would all be walking around super fit, but when we partner with an expert, we are held accountable and can feel more motivated to do the work.

No matter how disciplined you are, you can go further when you go together. Marshall Goldsmith is one of the top coaches in the business and even he has somebody that he calls every night so he knows he’s doing his ideal behaviors and can be held accountable. You can make it a two-way street and find a success buddy who wants to devote time to habit changes as there’s nothing more powerful than walking arm in arm with someone to go after your objectives. If it is the same goal like exercising more, you can take walks and workout classes together and even introduce a little competition to rev the engines. An accountability buddy allows you to report your goals, share your plans to get there, and help each other with information, connections, and motivation.

3. Recover from your mistakes. Let’s say you put in the most incredible systems, but somehow you get pulled off track. One crazy day in a busy week slams you and you are unable to do your exercise routines. It’s fine, you are human, the key is to return to the path. Because some people try to be perfect, when they break their chain, it stays broken, and the next thing you know you have been off your exercise routine for two weeks and now you do not know if you can resume. The answer is that you can always return at any moment. Be mindful to prevent a slip from turning into a downward spiral… first, you stop exercising, you feel sluggish, you have low energy at work, are unproductive with your assignments, feel irritable, don’t spend time with your family, and so on. Be patient with yourself, if you fall off the wagon, brush yourself off, and keep going. Try another strategy, reinforce your commitment, and press on. You got this!

Another reason why people get pulled off track is because they get to a certain level of success and then get too comfortable. We stop doing what we did to get us there and we slowly degrade like frogs in boiling water, warming so incrementally that they do not realize they are getting cooked.

5. Be quick to eliminate bad habits. A good way to think about habits is to think about cultivating a garden. There will be a variety of flowers, trees, and plants, which are the good habits you will want to nurture and then there will be the weeds, the unwanted habits, which should be ripped out before they grow too large. As Ben Franklin warned, it’s easier to prevent bad habits than to break them. Warren Buffet would agree as he adds “The chains of habit are too light to be felt until they are too heavy to be broken.” Taking a preventative approach can save you tremendous energy.

6. Permit yourself to break your routine. Routine and consistency are good, but sometimes the things that used to energize us can lose their effects. In that case, it is helpful to shake things up and interrupt your routines. Instead of going for a run every day, maybe you take a bike ride. When you deliberately take a break or challenge yourself with a new activity, it can reenergize your commitment. Travel is the ultimate activity because it forces you to do so many new things– figuring out how to navigate a city, where to explore, what to eat, who to meet, and so on.

7. Check-in with your habits. It is also important to recognize that sometimes habits have their seasons. Maybe you were intentional about eating oranges every day for 6 months but it is no longer serving you, so you can introduce another habit for another season in your life. Just because you decide to take one thing on, does not mean it is the thing you will do for the entirety of your life. Periodically check in with your habits to make sure it is the right match for where you are in life.

8. Reflect & celebrate. Evaluate your habits, what is going well, what is not, and what might need to change? Becoming the best version of yourself requires you to continuously review your behaviors and beliefs so you know you are spending time on the right things based on where you are. Comedian Chris Rock will test 100 jokes and record which bits went well in his notebook so he can repeat that specific behavior.

Reflections can happen at multiple levels - daily, weekly, monthly, and annual reviews so you can track your most important habits and measure your progress. Here is one way to reflect… on an excel spreadsheet, in the first vertical column, write a list of important things in your life, such as family, friends, and virtues you are cultivating. Across the top, list the days of the week. At the end of each day, complete the column by writing a simple yes or no. At the end of the week, review your scores. If you say your family is your top priority but they do not appear in your busy calendar and you have not checked their boxes, that’s valuable data for you to act on. It is only this reflection time that will allow you to discover the inconsistencies.

Don’t forget to stop and take the time to celebrate. Give yourself new rewards daily, weekly, or monthly. Read something fun, go for a hike, book a massage, eat the best icecream, or do any preferable activity that will add the benefit of disrupting your routine.

Some change is hard, but when we can create systems, enlist help, reflect, and celebrate our wins, we can make the process a little less difficult. And if it is still hard despite our best efforts, do them anyway, it will be a road you can travel to success.

Quotes of the day: “All our life is but a mass of habits.” -William James

Q: When was the last time you enlisted help to enact positive change in your life? What worked? Comment and share below, we would love to hear from you!

As a leadership development and executive coach, I work with people to cultivate habits that serve them, contact me to explore this topic further.

What’s your favorite tip for habit change?