Excelling with Difficult Employees

By Dr. Mary Kay

Updated Over a Week Ago

Minute Read

Difficult employees are the most difficult to reach and are often the eccentric ones, the extremely talented ones, or the rainmakers who bring in the customer base.

People who are often labeled “difficult people” are the ones that become our best leaders. Too many managers run off their best people under the guise that the person was not a match for the organization.

Managers are really missing a key strategy for gaining a competitive advantage. The organizations and leaders that become great are the ones that know how to make a difference with the eccentric types by smoothing their rough edges and developing their leadership skills.

Why Do Managers Run People Off?

Many managers don’t effectively lead strong-willed people as they often manage their tenacity right out of them. As a result, organizations lose their greatest people. They mistakenly believe that such people are unreachable and abrasive.

Because team members are not “yes people”, managers end up creating a gap in the relationship. They do this by ignoring them, talking over them, and often developing a dislike for them.

In turn, these team members question their manager’s efficiency matters are not being addressed. This is not a situation that will improve with time. But as a leader, you can make the changes necessary to create a culture where these problems do not exist.

You need to be a risk-taker and act upon the principles you know are right. Team members will see this as being proactive and having a high level of respect for you.

What Should I Do First?

To start, get over your frustration with these talented people by looking for what they bring to the table. Initiate a two-way conversation right away with them and find out the following:

  • Their goals
  • What generates passion in their life
  • Collectively discuss team expectations
  • What they need from you to succeed
  • What you need from them

As a leader, the key is knowing when to implement managerial authority and when to put more focus on “people issues.” The balance of leading and managing rests on your ability to develop as a leader while sustaining high-performing teams and individuals.

When to Lead and When to Manage

For many managers, this balance of leading and managing is difficult to achieve. Managers that react to difficult people get stuck. They let things go on too long by not addressing their organization’s most glaring issues.

They micromanage people with authority, use too many rules and mandates, and continually tell people over and over what to do. In short, managers don’t allow these potential leaders to choose their path to success or move on to their competitors.

Think about this: if the competitor knows how to make a breakthrough with your difficult person, they win!

Article Takeaways

Great managers use people skills when they communicate with all types of people by consistently being fair, frank, firm, and friendly. They let their employees know when they, the leaders, make decisions; those are requirements that everyone must fulfill without showing frustration. Team members appreciate this. They want their leaders to take a stand.

Leaders let their teams and individual members try to manage themselves. But when it becomes clear that the employees do not want to lead their own situations, the leader will manage things for them.

They will step in and clarify expectations in a clear, informative manner. In such a situation, the leaders’ responses are immediate. Their intent is to motivate and help.

Even though they are using their managerial skills and being more managers than a leader, for the time being, they can still allow team members to clarify things for themselves and provide their own input on the situation.

With this approach, there are no secrets, which alleviates the stress of having to discipline or even terminate an employee. When everything is upfront, and transparent, and interactions align with the core values of teamwork, those who do not fit in will weed themselves out.

Those who remain will move on to enjoy a clearer, more satisfying working experience where they know what they have to do and have the support they need to do it.

Reaping the Rewards

Balancing your leadership and management skills with difficult employees creates momentum and helps in getting ahead of the game. Your decisions at work will be concise, and you will not let people’s issues become stagnant or stuck again.

Most of all, you will work with the choices of your employees and create a well-rounded, well-oiled workplace that runs efficiently and smoothly.

The fun part is making a difference:

  • You have retained and developed outstanding leaders.
  • Individuals get to decide whether they’re going to be valuable contributors or not.
  • No blaming when things go wrong—only managing people’s choices.

How Do You Excel With Difficult Employees?

Have you had breakthroughs with difficult employees? Tell us about it by leaving your comments below!

Would you like to contribute a post?

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Dr. Mary Kay
Dr. Mary Kay
Dr. Mary Kay is a business leadership strategist, executive coach, trainer, author, and co-founder of the About Leaders community. She’s consulted with hundreds of companies and trained over 30,000 leaders. Her Ultimate Leader Masterclass helps managers become more confident, decisive leaders.
  • Duncan Brodie says:

    Excellent piece. I think it is always important to make the distinction between people who look at things differently from you and those who are difficult.

    In the latter category are those who go out of their way to stop anything happening.

    Some of the best people I have come across are often pretty tough characters and at the same time they deliver.

    I can recall one surgeon on our leadership team when I worked in the NHS in the UK who had no time for dithering and lengthy discussion. Unsurprisingly he was a top performer in one of the most demanding areas of medicine.

  • Dr. Mary Kay Whitaker says:

    Hi Duncan – Thanks for reading the article and adding to the discussion. To continue with your very important points, Ilike this thought, each of us is someone’s difficult person.

  • Al Gonzalez says:

    I agree with Duncan, this is a great article and we need to differentiate between those who come across as being difficult because of their different opinions and the small minority of staff members who will complain about anything, including a manager trying to set clear expectations and lead well.

    One the most helpful tools I have used in this process is identifying strengths via Gallup or Buckingham’s stregthsfinder tool. One of the first lessons is that if we don’t know we have a strength we could be “off balance” and this could actually be a weakness that may come across as being difficult. For example, there is a strength theme called Activator. People with this theme are good at getting things done and putting plans into action. However, they can also be impatient. There are others, this is just a good example around this issue. This is a great tool when the leader has to manage because the context of the interaction is focused on the fact that this is a strength that needs to be maximized. The process of maximizing that strength is to balance that Activator theme so that it is not something that actually prevents progress in working with the team. The difficult individual will realize that balancing this strength will actually help move things along and help her/him work better with others, which is good for the person.

    This model works well when themes are identified for all team members, including the manager, since we all can be difficult at times 🙂 It is great when team members start thinking about strengths when they are preparing to deliver honoring feedback. At that point, some of the managing is being done by the employees themselves,which can be very helpful.

    If a difficult employee gets clear direction and understanding leadership from a manager that includes tools like Strengths, Myers Brigs, Honoring Feedback, in the spirit of helping her/him and the team, but the individual keeps behaving in ways that negatively affect others, the manager then needs to continue the partnership with HR to handle the situation with other methods.

    While leaders need to focus on bringing out the best in all staff, there comes a point when we need to move on and work with those who want to work together, no matter how talented someone may be, if that person continues to negatively affect progress.

  • Stefan Tramontano says:

    When dealing with difficult people I always try to remember these 3 things:

    1) Two wrongs do not make a right. It is important not to respond to negative behavior with more negative remarks and behavior. Breathe. Try to look at the bigger picture and the overall goal and respond accordingly.

    2) Do not take things personally. People can only offend you if you allow yourself to TAKE offense. “sticks and stones”, remember?

    3) Stay flexible. It is always important to adapt your leadership style according to the situation at hand. Sometimes you’ll need a firmer hand, sometimes a more collaborative one.

    These have to do with interpersonal skills and using them to get the most out of your team.

  • I had the chance to work with a great engineer, the company let him go because he was this kind of difficult people. I was one of the only two persons who were able to work with him without any problem.

    The first thing that matter was to actually listen, not just nod and give no solution at the end. Second to give him reasons to reject whatever strange idea he could.

    I learned not to argue with him eveytime I disagree, just when it really matters. Once he was trying to teach me what I already knew for 10 minutes until he made his point, I let him talk waiting for the good stuff.

    It was a shame the company let him go, all the stuff he forseen became reality, it was not rocket science, it was just common sense that his manager was not able to see and pushed him to the edge.

    At the end, we have 2 ears to listen more and one mouth to talk less.

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