Dealing with Difficult People

posted by Administrator on 02/11/2022 in Blog Posts  | Tagged , , , , , , , , , , , , , , , ,
By: Tom Cramer


In an earlier discussion, we touched on the fact that, as a CEO, you will be faced with many tests of your leadership skills. One of those is Understanding the Challenges of Difficult People. Unfortunately, grasping the reality of difficult people being a fact of life is only the first part of that test.

Choosing Your Course of Action

Once you have objectively identified and evaluated the existence of a difficult individual in your business ecosystem, you face an additional assessment. It is generally best to eliminate those distractions and influences that impede the efficiency and esprit of your team. This can be a difficult process, as the board members who fired Steve Jobs discovered.

In the third of our articles on this topic, Eliminating Disruptive Influences, we dive into some of the steps you must consider when taking such action is the best option.

At the same time, there are situations when the individual creating a special challenge may not present you with such an option.

In those cases, another dimension of leadership is finding ways to make an imperfect situation workable. Even if they cause friction and take more time than you feel you have to offer, some difficult people may be important to your success. Proactively addressing the problem may not easily include getting them out of their position, at least immediately. These individuals may include:

  • A Co-Founder or stakeholder
  • Someone with special skills and abilities that can’t be easily replaced
  • An important investor or backer
  • A vital client or customer
  • A vendor who controls certain essential components or supplies

Even In these situations, however, you must still proactively manage the situation. One of the things that make difficult people such a danger to organizations is evoking emotions and reactions rather than objectivity. Left unaddressed, those emotions can evolve into situations that create untenable and damaging environments for you and your teammates. It can also create excessively negative consequences for that difficult team member.

You, as the CEO, have the job of creating the pressure valves in relationships if you are not able to eliminate the problem itself. There is a fine balance here between being an effective leader/manager and being manipulative to ensure the success of the organization. 

Pay Me Now or Pay Me Later

The easy answer of “just ignore that person” is never an acceptable leadership choice. If you have decided it is the best option to keep that difficult person around, or to at least try to make the situation workable, then it is time to develop an actionable plan.

The steps in addressing the difficult person who you can’t eliminate will depend on the specific situation and relationship. If it is an internal team member or stakeholder, you will find it helpful to:

  • Carefully plan for and meet with the individual to identify any definable reasons for the friction. It is surprising how many people do not realize they are creating problems in the workplace and respond to the well-reasoned presentation of the situation.
  • If specific root causes are uncovered in the discussion, such as a personality conflict or a misunderstanding of expectations, take action to resolve that issue.
  • Agree on the need for a change in the situation and set a specific timeframe for follow-up and assessment of progress. 
  • If the problem seems irreconcilable, it is time to turn to your advisors and develop a plan that addresses that specific situation.

If the challenge is coming to you from an investor, customer, or other external sources, it is just as important to not simply “grin and bear it.” Carefully assess what role you or any member of your team may play in creating that difficult relationship. 

Use a trusted and knowledgeable advisor to help you develop the best proactive plan to meet with that individual. With that plan, and in a constructive and objective manner, schedule a meeting to explain your sense of the difficulty and your desire to make the relationship more positive and profitable for all involved.

Once you feel you have made your best effort, you will either have an improved situation or you will know it is time to begin the process of finding a way to eliminate that hindrance.

The Takeaway

You, as CEO, must proactively address any difficult individuals who are impeding the positive forward movement of your organization. Even if they are in vital roles, a proactive effort will mitigate more serious future problems.