First-Class Coach

Q: I've been given a new role working for the CEO, developing new projects and initiatives. Although I've been told it's a good opportunity to show what I'm capable of, I feel insecure because there are no particular targets or deliverables of the job. I worry that there will be nothing to show for my work and that might make me vulnerable - although my boss has been very reassuring.

by Miranda Kennett
Last Updated: 31 Aug 2010

A: Congratulations. As one of the CEO's team, you have made it to the higher echelons of management. Uneasy as the vagaries of your new job may be making you feel, you have now achieved visibility at the top, and your appointment will reflect on your boss as well as you. As Machiavelli put it: 'The first method of estimating the intelligence of a ruler is to look at the men he has around him.' You owe it to yourself and the CEO to shine in the role.

As a sweeping generalisation, the world is divided into two groups: people who like to know, in some detail, what's expected of them, and people who are happy to have a much looser definition of what their job entails. For the first group, there's usually a desire to have some structure to their work, to be able to complete their tasks and be rewarded appropriately. For the second, the wider the boundaries of operation, the more new projects and the greater their autonomy, the better. Both groups have their merits, according to the circumstances.

It sounds as if you fall into the first group. The great benefit for your CEO is that he or she knows you can be relied on. Give you a task and you'll try your best to achieve it. Because you have proved able at tackling projects in the past, the assumption is that you'll be good at driving initiatives and troubleshooting in the future.

The downside for you is that not every issue or project may be as susceptible to being resolved or completed as the ones you have handled so far. At the initial stages of a new project, you'll need to establish expectations and define success in a way that is satisfactory to you and your boss. This may not be easy. Machiavelli also wrote: 'Nothing is more difficult to take in hand, more perilous to conduct, or more uncertain of success, than to take the lead in the introduction of a new order of things.'

I suggest you establish some ground rules with your boss. If he or she is a member of the second group, they may find detailed discussions of a new initiative tedious - after all, they've given it to you to handle because they're too busy or lack knowledge or interest in this area. So it's important to develop a shorthand methodology for this process of structuring expectations and providing you with working guidelines, confident in the knowledge that your efforts are not being expended fruitlessly.

Four questions must be answered. First, what priority does this task have? That can be judged by its importance to the organisation but also - to be Machiavellian - by its importance to your boss. Would this be a quick win, of longer-term importance, or so marginal that it's really a back-burner project? Use a scale of 1 to 10, or rank it against other tasks.

Second, what would be the ideal outcome of the work? Next, timing - what needs to be achieved by when? Finally, what resources are available to you - budget, people, equipment?

As your knowledge of the relative priorities expands, you'll be able to draft the answers to all four questions yourself and involve the CEO only for final approval. But at first, it will be important to go through the process with your boss. That way, they'll come to appreciate the tricky path you're treading. Make sure that when you complete a project or improve a difficult situation you get credit for it. And if, by any mischance, it all goes horribly wrong, you'll have a record of what you were trying to achieve and the agreement as to your operating parameters.

If you can get used to a less ordered, trouble-shooting existence you may enjoy a bird's-eye view of what really goes on at the top of your organisation. You'll also have a chance to sample a variety of challenges and position yourself for the job you'd like next. You might choose to return to a job with clearer objectives and chain of command, or find you've developed a taste for more loosely structured, multi-tasking roles.

Miranda Kennett is an independent coach. If you have an issue you'd like her to cover, e-mail:

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