Challenging Formidable Characters

Some senior people have a reputation for demolishing people in big meetings. Not only do they have strong opinions about the task in hand, they also exercise considerable skill in destroying any challenges to their opinions. Or so it seems.

This approach is often accompanied by a brusque style, blunt to the point of rudeness, and they have very high levels of determination. If you operate at middle to senior levels in any large organisation, you know who I’m talking about!

Challenging these people can be daunting. Nerves are an obvious problem. Being able to react confidently and quickly when they turn their focus onto you is really hard. And, on top of this, you also have the added complexity and pressure of the observers; either keeping their heads down or looking forward to the sport. If one happens to be an adversary, expect them to join in and stir things a little too.

So, if you want to challenge and influence formidable people, what can you do? Here are a few ideas to consider…

1. Check Your Attitude. These people are often misunderstood. They are not all bullying megalomaniacs with deep-seated insecurities. Many, in fact probably most, are extremely capable and determined servants of the organisation. They want and respect well thought-out challenges which help to build a stronger result for the business. So, take a look at the evidence in an objective way, and make sure you really understand where they are coming from and how they operate.
2. Determine Your Approach. Go deeper into how they work. Look for evidence of how they process challenge. What have they done with others who challenged? Who has been successful with challenging them? Why? Who else has failed, and why? Figure out a robust strategy to get you going, but please don’t include heavy reliance on the support of others during the challenge – you could well be on your own on the day!
3. Clear Decision. Make a firm decision that you will deliver a challenge. Weighing up the relative importance, risks, etc. is a vital part of the decision-making process. Half-hearted decisions are a recipe for disaster with these tough characters.
4. Meticulous Preparation. Any chink in your argument and they are likely to seize on it (perhaps unfairly). They will view this as symptomatic of your overall approach and this could lead to an early and final failure of your challenge – even if you are absolutely right. So, be thorough. Look around every corner, get it checked out by others. Consider - if you were in their shoes, what would your concerns be with your challenge?
5. Profit and Loss. Get real, if what you are proposing is going to mean they will lose in some way, be honest and hit it head on. Don’t try to hide it. Get it out on the table and have a clear argument towards why it is still the right thing to do. Indeed, short-term loss can easily translate into long-term profit, so you may need to stretch out the time horizon to help them see the light.
6. Adjust Your Style. If you tend to be more caring and considerate than they are, you will probably need to keep that in check for a short while and adapt towards their usual style. If their preferred way is hard drive and determination, they will not respect a caring and considered approach. In fact, they will probably dismiss it immediately and drive straight over you. So, you need to gather your courage together and drive hard with your objection/challenge, so they will take notice long enough to hear what you have to say (more information here.
7. Contingencies. Part of your preparation should also be planning what you will do if you are unsuccessful. Consider the possible outcomes and what you would do if each of them became a reality. Preparing other stakeholders in advance is part of this process. You may not want to get them involved directly, but keeping them in the loop ahead of a challenge is often a wise move.
8. Keep It Clean. If you try the head-on approach to challenge them and don’t win, don’t start to play dirty around them. Trying other more political approaches afterwards will quickly earn you a reputation for being a sore loser, moaning and groaning away in the background. Frankly, an irritation which could get wiped out completely when they have a few moments to spare. If you give it a good try, but don’t win, publically cut your losses and move on.
9. Be Careful. If they are indeed a bully, expect reprisals, particularly if you win. Feed this into your decision-making process. Challenging them could well be an extremely unwise move, irrespective of how right it is.

Yes, it’s hard work challenging formidable characters, and you don’t have to go in expecting to be successful. In fact, a solid attempt which fails can lead to a growing level of respect from them. They will start to see you as someone who is prepared to stand up for what they believe in and definitely someone to have on the team. One client recently told me about a time when she challenged with the opening statement, “Andy, I have to say I totally disagree with you”. As everyone else in the meeting ran for cover, he turned his full attention on her, smiled and said, “Great, tell me why”.

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