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How the Best Managers Keep Star Talent

The art and science of situational leadership

Matt Trainer
Jun 21, 2017 · 7 min read

he number one reason talented people leave companies is the failure of their direct managers. Companies live or die by the strength of their people. Even within highly successful companies, a bad manager can drive talented and promising employees to burnout, depression, and failure. Even managers with great intentions and a track record of success can accidentally tear up teams.

But there is a way to prevent these mistakes and create a thriving business while developing strong talent.

Successful managers apply targeted, dynamic coaching to each of their individual reports. There’s no single management style that works for every situation; instead, managers must adapt their approach to each employee’s unique situation. This approach is called situational leadership. It’s a method now taught to every Facebook manager around the world.


Tom’s Story

Tom’s story at Facebook seems like the perfect Icarus tale: success and excitement followed by a fall from grace and ultimate departure. But it is not a hopeless tale, and there is a lot that managers can do to prevent similar tragedies of wasted talent from affecting their own teams.

After several years of high performance as a technical partner manager within Facebook’s business development team, Tom was offered a job within the core product management team. He understood every detail of his product area and was skilled in planning, market requirements, and relationship management. He was a perfect fit for product management.

But even though Tom was a master of technology and business on his former team, he became increasingly stressed in his new role. Tom’s self-doubt intensified, he began missing deadlines, and he eventually fell into a full mental breakdown. Within eight months of joining the product management team, Tom left the company.

Today, Tom is the CTO of a successful startup, and he’s thriving in his role while his company regularly gets acquisition offers. The truth is that he didn’t fail at Facebook because of his own faults, but because of his lack of proper management.

I was Tom’s previous manager in the business development team. After two years there, he needed very little direction or encouragement and often designed his own projects and goals. When he moved to product management, Tom’s new manager gave him very little training or encouragement and let him set his own agenda. That’s when Tom fell apart.

So why did the same management technique work for me and fail for his new manager, despite Tom being his same intelligent and productive self?

The difference is in Tom’s stage of development in his role. On my team, Tom was a veteran accustomed to his tasks and confident in his skills. Despite his knowledge, however, product management was new for Tom, and that’s where he needed a more directive and supportive management approach.

Situational Leadership

Paul Hersey developed situational leadership in the 1960s. His goal was to develop a model that helped all kinds of leaders influence others. Since then, this model has been deployed across 70 percent of Fortune 500 companies and received numerous awards from training experts.

The model works by clarifying how we learn new skills. All of us — highly competent or not — go through four general stages of mastering new tasks. For each of these stages, and specific to each task, managers must adapt their approach to managing their report.

It all depends on the employee’s relationship to the specific task they’re trying to accomplish.

The honeymoon phase.

Stage 1

When someone approaches an unfamiliar task, they begin with eagerness and determination — they see a bright future and lots of learning opportunity — but they are complete novices in execution. They are high on motivation but low on skill.

In this situation, the manager will need a highly directive approach, where they show the person how the task should be performed, set concrete goals, and closely review progress. The manager will need to do very little initial encouraging, because the person is generally in the “honeymoon” phase and able to sustain their own energy.

Many managers fail to support the growth and training of their people because they think they’ll seem like a micromanager. Micromanagement is a common negative term in the business world that reflects an overbearing and restrictive environment. But sometimes people need training wheels, and they can grow faster when they’re shown more specific do’s and don’ts of their work. Like a master to an apprentice, a manager who invests in strong training will create lasting impact on their employees.

In Tom’s story, he could have used more support while he built his skills. Training and guidelines are highly appropriate ways to give new employees a strong foundation for future growth.

The trough of despair.

Stage 2

The second stage of development is often called the trough of despair. Because it generally takes much more time to master a new skill than people expect, discouragement sets in as they lose confidence in their ability to perform well. They have built up some skills and knowledge, but their confidence is at an absolute low.

Learning takes time, so the manager’s role in this period is more of a salesperson or cheerleader. The manager should remind their report of why the person was chosen for the job, why they wanted the job in the first place, and how far the person has already come in their development.

In Tom’s example, he needed his manager to encourage him and stay close to his development as he reached his 30- and 60-day mark on the team. While Tom needed less direction than a first-day employee, he still needed more feedback than the average product manager, and positive reinforcement was more important than ever.

The confidence climb.

Stage 3

In the third stage of development, people have generally gained enough skill to be competent in their task but still maintain a mentality of imposter syndrome, meaning they are more skilled than their confidence level reflects. They might even feel like they’re still in the trough of despair.

At this stage, the manager should do less guiding and supporting the employee and instead allow them perform and self-direct more consistently. These acts of trust from the manager boost the employee’s self-esteem. At this stage, the employee’s dependence on their manager slowly fades as their own confidence grows.

In Tom’s story, he never made it out of the trough of despair. It wasn’t until he moved jobs that he was able to rebuild his confidence, and with his departure, his manager had to invest additional time into hiring and training a new employee, all while suffering decreased productivity. The failure cost both Tom and his manager significantly.


Stage 4

People reach stage four when their confidence rises to match their skill. From that point, they are the veterans we all know — wise, capable, and self-assured. They will continue to grow both in confidence and skill, becoming true masters of their craft.

At this stage, the manager’s role is to ensure the employee has plenty of room to continue growing. The manager ought to check in and ensure the employee is facing new and bigger challenges, and then recognize the person effectively for accomplishments along the way. This is definitely where micromanagement is inappropriate, as the employee really wants the freedom to apply their skills in creative ways.

Today, Tom manages a large team, proudly teaching what he knows to those he mentors and leading his team and company toward success. While I’m proud of what he’s built in his new role, I’m sad that Facebook lost such an inspiring contributor.

Your work as a dynamic manager.

Taking It into Your World

When someone is in distress, they feel alone. They rarely see how their problems relate to what others around them have experienced. Distress can strike us at any stage of development, whether we’re feeling in over our heads or micromanaged, or when we’re independent but neglected.

I regularly have conversations with my reports in which we talk openly about the stages of development and where we feel they are. It’s a universal framework that helps them realize that they are not alone, that growth is something we can work on together, and that we have a common language for sharing our experiences and expectations.


It’s especially helpful to use this framework when a veteran is beginning something new, which is why I told Tom’s story. People who are used to easy successes can be jolted by the struggles of something new, and this applies to managers as well. When we have smart people, we should support them through growth in ways appropriate to their level of development. We need to watch for signs of struggle and probe for the truths behind people’s polite answers.

When managers apply adaptive and targeted guidance to each of their people, those people thrive, and that’s the kind of environment where strong performers want to work. If you’re a manager, it’s the kind of environment that you are responsible for building.

Better Humans

Better Humans is a collection of the world's most…

Thanks to John Yi and Coach Tony

Matt Trainer

Written by

Head of Facebook Partnerships Program Management by day. Writer by night.

Better Humans

Better Humans is a collection of the world's most trustworthy writing on human potential and self improvement by coaches, academics, and aggressive self-experimenters. Articles are based on deep personal experience, science, and research. No fluff, book reports, or listicles.

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