The Delicate Dance
For many, it’s the final frontier. The line they dare not cross.
Every other difficult conversation they will get to at some point, sometime. But not this one.
I am talking about the conversation that offers a direct challenge to your line manager, or the boss.
This might be about a decision you did not like, an unkept promise or even the ENTIRE DIRECTION OF TRAVEL for the organisation.
Let’s not forget, your manager needs you to be good at this, but it does not mean they always appreciate it at the time.
You need to be prepared, calm, box clever and hold your ground while stopping short of complete insubordination.
How to dance so delicately?
Here’s four ‘how tos’ to consider.
1.Prepare the ground
Do not go into this conversation cold, particularly if it is the first time you are having such a conversation with this particular line manager. A spontaneous outburst may not do you any favours, at worst backfire horribly.
Find out from your colleagues how such a conversation may go down. You are unlikely to be the first. Ask them for tips on how to handle it.
Test out the points you want to raise on them. Far better that they spot the holes, before you find your argument being dissected at length in a discussion you wish you had never started.
The clues for how to handle it are often there in other interactions. What happens in a meeting when the disadvantages of your manager’s proposal are raised? Do they bite back or listen carefully? Do they invite genuine dialogue, or does consultation mean waiting for you to agree with them?
Some managers are very thin-skinned, particularly on certain topics. You need to anticipate what the reaction will be as far as possible.
This will inform you as to whether it is something you raise in a team meeting, with strength in numbers and witnesses around you, by email or if you put your head around the door on your own and ask for five minutes without advance notice.
Ultimately, you will have a decision to make as to whether it is ‘worth it’. If you find the issue gnawing away at you, pushing at your values or ethical boundaries then you know you need to raise it.
It is worth taking a little time to test out your own feelings and arguments. If you sleep on it but keep coming back to the same problem, it is time to make a move.
2.Demonstrate alignment
It is much easier to instigate a difficult conversation if you have proven yourself over time.
I am not necessarily talking about this in terms of performance, although that is always helpful.
Ultimately both you and your manager work for the same organisation. In this respect it does not matter that they are more senior to you, or if they are the CEO. You are both on the same payroll.
Starting a difficult conversation is much easier if you have established enough credibility that you are in the job for the right reasons, and that you operate in a trustworthy manner.
If you consistently do what you say you will do and are transparent about setbacks or challenges, you can establish trust and credibility with your superiors. Your integrity, like your manager’s, depends on demonstrating your commitment to the organisation’s goals.
You need to be seen to be in it for the organisation and not yourself. It does not help if your knock on the door is met with a ‘what does this person want out of this?’ If your manager’s suspicion is that the answer to that question is their job, expect short shrift whatever your intentions.
You need to demonstrate that you are aligned with the organisation's overall priorities and strategic objectives. Be ready with examples of how the points you want to make will contribute to the organisation's mission and goals.
Then you have a strong chance of a fair hearing.
3.Help them manage upwards too
This is seriously underrated, particularly if your boss is the CEO. You are not the only one who has to manage upwards.
Often senior leaders only see the organisation chart to which they belong. They do not look at the chart(s) their manager is part of, where they are not top of the tree.
Furthermore, they may not consider all the stakeholders their manager has to engage with; strong functional relationships play a significant part in their overall success.
In short, too few senior leaders take the opportunity to see the organisation through their manager’s eyes. Your prospects of a successful conversation are considerably higher if you at least try to do a bit of that. Not only does it indicate an interest but it also will help you see your own role in a broader context.
Wherever your line manager sits within the organisation they will be accountable to someone. A senior manager reports to the CEO who, in turn, reports to politicians, shareholders or a governance arrangement (and occasionally all of them).
They may spend more of the time than they would ever admit being concerned about what they are asked to do, the way they are asked to do it or what will happen to them if it does not work out. The further up they are the greater the responsibility and accountability if this proves to be the case.
By raising the issue you may be helping them solve their own problem. Through managing upwards as a direct report you are modelling a process which your manager can replicate for their own benefit. They may be more grateful you have raised the issue than you realise.
4.Be ultra-clear on the impact
What you think does not particularly matter. If this was just about opinion sharing, you may have already had the opportunity to contribute.
You need to show that you have really thought it through, found the precedents and collated whatever concrete evidence is available. There is a big difference between doing your homework to discover whether your hunch has something to it, or campaigning for a change because you want to score points.
Ultimately, managing upwards IS leadership. This requires you to consider the impact of the change you want to make in full.
Discussing the impact is invariably the key part of any difficult conversation. Often it comes down to the impact on an individual, the hurtful words or your proposal which got thrown out.
But if you can demonstrate the likely impact of the problem across a range of perspectives and in the long-term, you will strengthen your argument.
The quality of your argument will be all important. Whether it cuts through or not, if you have prepared thoroughly and handled the conversation well your candour should be appreciated.
Remember that
Managing upwards is part of your job, like it or not. The longer you duck it, the longer you are abdicating your own responsibilities.
The conversations you instigate may be some of the most rewarding. It can be where breakthroughs are made, and your potential realised. Think it through, then make your move.
How can I help you?
1. One to one coaching programmes for senior leaders who are swamped by their jobs so they can thrive in life. Click here to discover where you are on your journey from Frantic to Fulfilled? Just 5 minutes of your time and you will receive a full personalised report with guidance on your next steps!
2. Team coaching programmes - working IN a team is not the same as working AS a team and yet they are often treated as if they are the same. I help teams move from the former to the latter, and generate huge shifts in productivity and outcomes.
3. Talks, workshops and seminars - including topics relevant to the two areas above plus explaining Gen Z to Gen X.
