Dealing with Difficult People

Dan Springer, CEO of Responsys, speaks with graduate students at Stanford about dealing with difficult people. He shares an interesting view – one that most of us will recognize from experience.

Dealing with Challenging Employees

Many leadership courses begin with the ideals of leadership that focus on building people and helping people get to the next level in their personal and professional growth. However, some of the most frequent leadership questions are:

What do we do with people who just don’t fit?


What do we do with people who need tough coaching?

Deal with People Head On

Do not delay facing the situation and do not try soft workarounds like dropping hints to the person who is a problem and hope they will somehow change. 

Reason #1

The first reason for taking a problem head on is to help the employee. It’s never fun to have to be direct about a negative situation with a person. However, great leaders manage with courage, which requires that they step out of their personal comfort zone and professionally address a problem in a direct and timely manner. Failing to manage with courage hurts the individual. When the leader doesn’t directly address a problem, the person with that problem will carry it into the future without fulling understanding the implications. A good leader thinks about the future of the people they lead. That means they take a long-range perspective and are willing to help individuals develop their potential by coaching them up in areas where they are deficient. 

Reason #2

The second reason for taking a problem head on is to help the team. Failing to manage with courage and address a problem when it needs to be addressed creates an unhealthy organization. Teams organically adapt to accommodate each other’s behavior and work styles. When a person is deficient or has unacceptable behaviors, and is never corrected, the team’s work-life social evolution will factor those behaviors in and inherently create sub-cultural accommodations. In other words, bad behavior or sub-par competence is now being built into the culture, which means it will become sustained. It also means that morale will be lower than it should be and team performance will not be as high as it could be. The culture becomes accepting of a co-dependent atmosphere.


To help everyone, involved leaders need be direct and deal with problems head on.

Treat the Situation with Dignity

People matter – even people who are challenging to deal with. 

When preparing to communicate bad news to an individual take the time to understand their perspectives prior to the meeting. This concept is true whether you are communicating to the president of the company about a business breakdown, or to an employee who is going to be part of a downsizing event. Trying to understand the perspective of the other person in advance, gives you the advantage of developing your message in a way they will be able to absorb and act on. 

Protect Confidentiality

Do not share private discussions or the results of those private discussions with others who do not have a professional right or need to know. When we violate perceived or real confidence it gets around – people ultimately always find out. When confidentiality is breached, not only will those involved be upset but everyone else in the organization will also be negatively affected. Your reputation will be damaged and trust in you will falter. When a leader cannot be trusted to keep private matters private true team or organizational high-performance cannot be achieved.

Use HR

One of the modern strategies of the Human Resources industry is to become an impactful business partner. One of the ways many companies implement part of this strategy is to assign an HR partner to a business unit or division. Whenever a line-level leader is involved with a human resource issue it is very wise to consult with your HR partner. Staying connected with HR will help in the following ways:

  • Following company policy and best practice.
  • Understanding and complying with legal requirements.
  • Collaborating in confidence with someone who is trained to provide insight and advice on complex human resource issues.
  • Providing confidence in how to proceed, to include having a checklist of items to consider prior to taking any serious action.
The Wrong Way

Leaders247 Founder Gordon Whitehead shared this story:

When I was a young manager at a very large company we had a tough situation. An average performer, who was really well-liked, had a severe hygiene problem. The problem kept him from being effective with customers and his peers. For some reason nobody noticed it through the hiring process and now nobody wanted to address it. One complication was that this person was a minority. At that time in our company hiring minorities was a component of the manager’s performance evaluation; managers were given points based on their diversity scores. This had the effect of making it even more difficult to talk to a minority about a sensitive problem such as hygiene.

This particular individual had bad breath, which made it difficult for him to deal effectively with other people when in meetings or close quarters. This person also did not understand personal space and usually got just a little too close to people when he spoke with them.

Our leadership team met about the issue. Nobody quite knew how to deal with the problem. Suggestions ranged from take no action, to leaving a tin of Altoids at his desk as a hint, to having a direct conversation with him. 

What happened? The leadership team debated, discussed, and strategized, but no action was ever taken. The person with the hygiene problem never found out what people really thought and he continued in the company just as he always had. The result: He never rose to a higher position, he never received exciting assignments, people were polite, but did not want to work with him – he was simply tolerated.

This story’s lesson is a sad reflection on what happens when leaders do not address difficult situations head-on. They hurt the person, they frustrate others involved, they slow down team progress, and the company does not benefit from the full capabilities of its people.

The Right Way

If we could go back in time and replay that story the correct thing to do would be to have the manager sit down with this man and have a direct conversation, treat him with dignity and respect, and then protect his confidentiality.