Some days are just bitter and grey. I need to finish this boring task that seems to take forever because of this bloke who is just so unhelpful that it borders on sabotage. Whenever I ask him to give me access to the right data he comes up with excuses, other priorities and such things. After I tried today for the nth time I have finally got the paperwork from him to fill in to get the right permissions - blimey, he could have given me it right the first time round (am I really happy about getting paperwork?).

In our professional work life we regularly come across difficult people we’d love to avoid, ignore or get away from - this is especially true if you are a consultant or contractor and work with so many different people. Usually however, we can’t do that: we need to work with them as productively as we can. Even if we don’t work with a difficult person everyday, we may need to convince them of something from time to time or get some output from them. Dealing with difficult people is obviously a challenge which everyone approaches in a different way.

Being the structured (and enthusiastically chaotic) person I am I like to think about it analytically. Taking it step by step, I first want to talk about what kind of difficult people and types of situations are out there. Then, let’s think about strategies for dealing with them.

Types of difficult

  • There is the team mate who is just not doing things as the team agreed.

  • The project manager interfering with the team, falling back into command and control mode and trying to force the team to do specific agile experiments.

  • It’s the DB administration team not letting the project team deal with the dev environment database changes but instead wants lengthy documentation defining each single change. They are also a bottleneck with a 6 week waiting queue and they will only change their priorities with senior management intervention.

  • It is the vendor test analyst that constantly argues that any bug raised is actually only minor because a workaround exists - no matter how intricate it is.

  • The client project manager that always wants the team to cut the estimates because he expects them to be ‘experts in the field’.

  • The project sponsor coming in with the whip of enforced velocity targets that have not even been derived by any meaningful technique - asking for constant overtime to meet them. All the while the quality needs to be top notch, of course.

  • The travel department escalating travel costs to a small fortune without telling you beforehand and giving you the chance to tell them how to book it much more cheaply.

  • Or the guy calling you asking you to identify yourself to him with lots of personal data without any willingness proving his own identity.

The list could go on and wouldn’t even get boring by the tenth page. After the fact this all tends to be quite funny, we share impossible anecdotes and laugh about it together. However, in the moment these situations are never very funny but instead rather infuriating, mind-boggling, perplexing or just plain silly.

  • It can add complexity to the situation dependent on how we relate to the difficult person:

  • Team colleague of the same company

  • Team colleague of a different company, e.g. a client/vendor consultant or a contractor

  • Someone in a different team

  • Someone in a different department

  • Or even someone in a different organisation including for example a regulatory authority

  • It could be a superior, your boss or just someone else up the corporate hierarchy

  • Someone you are supposed to be leading or managing, i.e. you are responsible or accountable for their work

  • Or an employee you are line-managing

Some simple observations

This is basically a tour around a typical organisational hierarchy - people in all places can be difficult. Interestingly enough from my own observations it usually doesn’t help if you are formally in a higher hierarchy position or even line-managing the person in question. I think it is really important for everybody to realise that

anybody in a company can just say ‘no’ - and there is not much you can really do about it

using any kind of authority. This is so because people saying ‘no’ (or being difficult in another way) have usually reasons why they are difficult. That is actually another interesting fact:

Virtually nobody is difficult without a reason that makes their behaviour perfectly sensible from their own perspective.

There are certainly also personality traits that make collaboration more difficult but mostly it is not one trait but instead two that clash. For example the controlling personality working with a self-organising agile team, or the rule following person in the midst of an agile transformation clashing with the rule breaker. This leads us to the right kind of question to tackle the debacle:

Why is that person acting difficult?

We can try a lot of things when dealing with difficult people, try to convince, coerce, use another’s authority with an escalation or make some kind of a deal to name a few. These things can work but they rarely have great outcomes, at best we get a mild form of consent at worst the person says ‘yes’ but does not buy in or maybe doesn’t even do what we need them to do maybe offering only some flimsy excuse later on.

A way forward

So, what better way is there? Fundamentally, we are talking about a situation where two different needs exist and both needs are understood in two different ways. If we want our need to be fulfilled we have to communicate the need and our reasons for it properly. However, our explanation will always be filtered by the perspective of the other person. That means we should first try to understand that perspective so we can predict the filtering. This should be our starting point even before we talk about our needs. However, this is not a simple thing as we don’t know what exactly might affect the others opinion with regards to our specific need. Some things we should consider are:

  • Are there specific ways of working that person needs to comply with?

  • Is there a lot of pressure on the person?

  • Which expectations do they have on their own duties?

  • What impact does our need have on them?

  • Are there important personal circumstances like a recent or ongoing illness?

  • What culture is the person coming from and what impact does that have on the way they work and communicate?

  • Is the person afraid of certain things, do they feel comfortable with their role?

  • What is the person’s current mood - is there a specific good and bad time to approach them?

Relationships galore

This is just an example list of things to consider - there are many more to look out for. It is evident that we cannot just use a checklist and go through it in a conversation. Instead we need to build an ongoing professional relationship to enable us to understand the other person. That means we have meaningful conversations regularly and we treat the other person with respect even if we occasionally cringe inside or even need to agree to disagree. If we have a working relationship we only need to look for the specifics of one situation and approach the conversation with the right clarifying questions. An ongoing relationship also means that the other person understands us better over time and we gain trust.

Why not just ask?

Sometimes we will still not get the reaction we are looking for. It is important then to check with powerful open questions why they are reacting in this way and to make sure the message you were intending to get across has arrived undamaged. If you need someone to do something to fulfil your need it is more powerful to explain your need and ask for their help instead of asking them to do something that fulfils our need. That way they can come up with a solution to our problem that suits them, we get much more buy-in because it is their idea and not us pushing something on them. Even if we try your best, friction can still occur. The other person might still not be helpful. Hopefully we will at least understand better why - enabling us in turn to look for other solutions or getting the right kind of help. Often it can help to ask how to get the person’s support such that they are able to help. Maybe they feel not empowered to change their priorities or they don’t have the confidence to do the task.


If the person remains unhelpful despite all efforts we sometimes need help from a superior, e.g. to make a decision enabling the other person or to clarify if the difficult person should really just get on with it - to name just two possible reasons. If we are considering an escalation we should be well aware that this is going to add pressure on the person. It is important to check if that will actually be useful for your cause and if so you should let the person know that you need to take these steps - not to use it as a whip but just out of fairness. In the end we still need a respectful relationship with them at work - even if they are unhelpful for us. Revenge, open fighting and shouting, swearing at people are all unacceptable and will never help anybody. If our temper gets us we should apologise for any unacceptable behaviour or harsh words. That doesn’t mean we need to suddenly get all cosy with the person but professionalism is a necessity for all of us.


The key to working together in a constructive and trusting way is to be genuinely interested in the other side: we need to understand our co-workers, their needs, opinions, preferred ways of working, mood, communication types and so forth. Respect, honesty, transparency, fairness are just a few key values we should always aim to follow for healthy and fruitful relationships. We always need to be careful about violent communication - it is very easy to unintentionally hurt someone with words. Whenever we communicate with someone - especially someone who we don’t know very well - we always need to keep in mind that they may misunderstand us in a bad way. In the end we should always remember that sometimes we are the difficult person - maybe even without realising it.