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When you are a strategic adviser to a senior leader, often the biggest challenge is knowing what type of behaviour is expected in a given situation. Get it right and you can really make an impact. Get it wrong and you can set back your career. To help navigate these complexities, in celebration of the Wimbledon Tennis Championship, here is a guide to the different types of advice senior leaders expect from their counsellors, and how to recognise each situation.

Wimbledon has a simple format: people battle it out for victory until there is only one left at the top of the tree. This person is usually called Federer or Williams. But there are plenty of supporting cast members – strategic advisers if you will – along the way who all contribute to making the tourney a success.

Here are 4 things leaders ask for and how you can react.

1. “Help me/us win in the marketplace.”

Your leader wants to win. Therefore you are Severin Luthi or Ivan Ljubicic – Federer’s coaches. Who? Exactly. Few outside the profession have heard of them. Yet, their skills as advisers have helped achieve what few realised was possible.

In tennis, ‘winning’ is easily defined. In the corporate world, you need explore what this means in practice, translate it into SMART goals, and develop a project plan to get things there. You’ll get buy-in from the leader and work to align the whole team around the agreed goals.

No doubt there are times when the coach has to communicate a tough message; or make Roger do something he doesn’t want. But if you have agreed the overall goal, and the steps required to get there, it is easier to deliver strategic advice.

2. “Make me/us look good.”

When you get a request like this, you need to channel Greg Cantin. He’s the Head Groundsman at Wimbledon. Again: an invisible hero.

There is so much more to this request than meets the eye. In effect, your leader is asking you to apply all of your experience. No one will notice if it goes right, but if suddenly – if something goes wrong – some weeds, a divot, a crack in the surface – you will get the blame. Your stakeholders expect perfection every time. Therefore, your challenge is two-fold.

First, you need to find a way to manage expectations. For example: everyone knows that the quality of the grass will deteriorate during the Championship. As an adviser, your role is to have the conversation about the likely outcomes and help have a discussion about the trade-offs involved: how much wear is acceptable?

Second, you need ensure that your team’s performance and contribution is recognised. Your team won’t automatically get the credit – expect maybe an ironic cheer when they take the covers off after rain. So your job is the ensure they feel connected to the wider mission so they say: “I’m not just mixing the compost, I’m helping create a successful Championship.”

3. “We need delighted customers.”

At Wimbledon, the answer is simple: strawberries, exciting tennis, and perhaps a plucky local hero who over-achieves. Only some is predictable. You need to be ready for the ambiguity and the unexpected.

The challenge is to be ready to take advantage of the situation as it arises. If our ‘plucky local hero’ surprisingly makes it to Round 4 and her match is originally scheduled for Court 22: ignore the plan or formal process / rules and move her game to Centre Court to keep customers happy. Sounds obvious.

But to do this successfully, you need trust with your leaders, and the willingness to take responsibility, knowing you will make some stakeholders unhappy. Remember: if you promote ‘plucky local hero’ match to Court 1, you will need have a hard conversation with ‘aging veteran, used to be good but a bit past his best and well-known for his temper’ about why his match is suddenly on Court 22 with an equal number of spectators. Being a strategic adviser is about making these trade-offs and having the hard conversation.

4. “Is that your professional advice?”

Now you get to play Umpire. Perhaps you work in Investor Relations or Public Affairs where there are strict rules on what you say or do. Your job is to know the rules inside out and make sure that others are following them.

At Wimbledon, the Umpires sit on high chairs. They have a different perspective. Sometimes as a strategic adviser you need to do this – take a step back from the hurly-burly of the day-to-day and go and sit in the high chair and see what things look like from there.

As ever, there are some challenges.

First is the “Dr. No” problem. If you always retreat quickly to the law or the rules, then you risk being seen as a blocker. The ‘rules’ are your ultimate backstop but if you use them as a first resort, then you will be seen as inflexible, unhelpful, and unreasonable. If you can, use other influencing approaches first.

Second is the “John McEnroe” problem. How do you deal with a leader with a temper who shouts “you cannot be serious” whenever you make a decision they don’t like? These leaders might think they are above the rules. Perhaps their track record makes them think they can get away with it. In tennis, the Umpire can impose fines. This is harder to do in real life so your role as an adviser is to be calm and help your leader back down – without losing face – from their impossible position. This requires high level influencing skills which is probably a topic for another column.

There are plenty of other corporate challenge and requests. Indeed, if you have other corporate challenges that you would like explained through Wimbledon archetypes, please get in touch or leave a comment and we will do our best to reply.

Meanwhile, if you want to play “Wimbledon” with your team – and help your Federer or Williams through to success, click here to find out how you find out what it takes to lift the trophy.