How to Disappoint People

You hate to disappoint people.

It’s one of the key, raw parts of working life where you run into situations that require you to do it (or at least, strongly consider it). It’s very tempting and often quite doable to avoid it – either by not representing your side in negotiations when you really should, or even avoiding the conversation entirely.

This applies in many situations, for both managers and technical leads - for both folks, you run into situations where you’re either negotiating a direction, or even communicating the outcome of a decision or direction, where you know people might not like it.

For example:

  • You’ve decided to deprecate some infrastructure or code, or reduce support for it.
  • You’ve made a decision on your roadmap, that specifically excludes a certain requested feature.
  • (For managers) you’ve made a decision on performance review paths forward, be it around scoring or around action planning.

Most decisions you make, if they’re decisions of consequence, involve someone being disappointed with the result. If you’re satisfied that you’re making the right decision and are doing the right thing (you should be!), then the outcome that’s within your control is how you communicate that to people who care.

Disappointing in Advance

The soundbite I use when working with individuals and groups of leads tends to be some variation on “Always disappoint people in advance”.

Disappointing people in advance is almost always the best way to disappoint people. There’s almost never a good reason to delay communicating a disappointing decision to people who care about that decision, and when people find out is one of the few things that are directly under your control as decision-maker.

So, in a choice between folks finding out before they see the outcome of a decision and seeing it as it happens, generally finding out sooner is better. These can be awkward conversations, as it puts the pressure back on you as the decider to maybe revisit the decision (as it’s not seen as ’too late’). This is one of those crucial conversations where you have to defer to your own authority. This can be awkward to do, especially for new leaders and managers. You might be talking to someone with whom you have an otherwise good relationship. You might be talking to someone who you know isn’t going to take bad news well.

However, the other side of this equation is how you’re seen as a partner and collaborator. This is from the point of view of the stakeholders for your decisions/directions/roadmap, but also from the point of view of your own team. You can be seen as inflexible, or too flexible, and the opinions differ based on where you sit. A leader who is seen as a ‘good partner’ by other teams and organisations might be seen that way because they always bend over backwards to be amenable, which can be at the expense of their own team’s capability.

You want to, above all else, be consistent. You are setting an example to your team for the style of leadership you want to be seen to be practising, so that they will hopefully emulate it in your absence. Similarly, you also want to have your partners in other teams know your mind, and be able to emulate your “Giggle test”. If you’re unpredictable, either by being too inflexible, or by being amenable to flip-flopping when pushed, you end up having a lot more low-quality conversations over time.

In a situation like this, it’s often helpful to put yourself in the shoes of your team and your partners. Given the choice of finding out about something you don’t like before rather than during/after seeing the outcome of it, which would you prefer? And in a more long-term sense, which options makes you more able to plan and in turn be predictable to your own partners?

No Surprises

This applies moreso to longer-term conversations, such as with your team as a manager. If you have a longer-term narrative going on where you’re discussing performance or giving feedback, it’s never a good idea to surprise people. The outcome of performance management should never be a surprise, it should form a cadence point in an going, two-way conversation between someone and their manager.

Speaking of soundbites; the one I use that covers most performance management “Dos and Dont’s” is “No Surprises”. If you keep this in mind, it covers many of the more awkward conversations and spreads that out over time – they are often still awkward, but removing the element of surprise from performance conversations results in better outcomes overall, and takes the edge off what may be a disappointing conversation at a point in time.

Similarly, if you’re consistent in how you approach decision-making as a leader, and how you communicate and stick by your decisions and directions, you end up with partners and a team that see you as someone who is credible and a good partner. Even if you sometimes don’t do things their way or take decisions that don’t go their way, the predictability of hearing about things early, and ideally as part of an ongoing narrative, will set you apart in people’s minds moreso than any individual decisions might.