Saying No Nicely: Challenging Conversations

Last week I talked about the importance of putting first things first, to prioritise progress.

But here’s the thing with priorities. Setting them is one thing – sticking to them is something else. The best laid plains go awry, and it can often feel like we’ve only just agreed on a new direction before we’re making exceptions and taking on something else.

I ran a great session in Auckland last week, where we did a ‘Marie Kondo’ of strategic plans and collateral – dumping them all in the middle of the table and then working through the pile systematically to discard everything that no longer aligned with the future direction of the team.

This was tough work.

Saying yes to something new is exhilarating – full of possibility. We dream of a new future, unencumbered by the things about our current state that make progress a challenge. 

However, the uncomfortable and non-negotiable consequence of saying yes it the inevitable no. Saying yes is a temporary, one-off moment. But what it kicks off is a longer, fractured reality of saying no, letting go and moving forward, triggering all the inevitable loss, confrontation and tricky choices needed to get there.

In ‘Necessary Endings’ Dr. Henry Cloud uses the beautiful, poignant metaphor of a rose bush, to emphasise the importance of letting good go to make space for great. A rose bush produces more life than it can possibly sustain – putting the onus on the gardener to carefully cultivate this life, in order for the bush to reach it’s full potential. Directing enough nourishment and energy to the great buds requires culling those that are unlikely to yield the best results.

This is true for the existing buds – like the pile of strategic collateral on the table in Auckland last week – and for new buds, that continue to emerge and need to be carefully examined. It’s hard, to acknowledge that some buds need pruning. It’s even harder to prune new ones before they’ve had the opportunity to grow.

The alternative, however, is to keep piling on – and watch a potential future suffer. Everything you say yes to comes with an opportunity cost. This cost might be resources, it might be your time and attention, or ultimately your health, values or potential for impact. The fortitude and commitment to confront these trade-offs is the number one skill of a strategic leader.

Manifesting this commitment is difficult, which is why cultivating this ability will set you apart as a leader with strength, integrity and vision. Breaking through the hardwired impulse to seek approval from our peers and superiors is no easy feat! But it cannot be avoided, in the pursuit of meaningful impact.

Your commitment will require challenging conversations – now, and on and ongoing basis. Some of these will be easier than others. When people you respect, or report to, confront you with a new request or direction, you face the discomfort of pushing back.

Which is why pushing back on requests, timelines and emerging options requires more than fortitude. You will need a clear, practiced suite of key messages and a palette of language that redirects the ’asker’ and realigns your discussion to the bigger picture. 

In my new book From Strategy to Action: A Guide to Getting Shit Done in the Public Sector I talk about how to push back when the requests come from senior leaders and decision makers.

Respectful, consistent conversations will ask questions like:

Is this more or less of a priority than x?

How does this fit alongside x and y? 


These questions change the agency dynamic, politely requesting the deeper consideration of the big picture from the asker. Even more powerful than questions is the provision of options, which make the consequences of trade-off clearer to those asking for new action. Options provision might sound a bit like this:

To get this done means something else will need to move. Would you like me to push out the timeline on project A, or reduce the quality on project B?

One of the Chief Executives I work with uses a great shorthand like this for communicating with politicians like this. He asks: Do you want me to do an A, B or C job? 

For totally left-field requests, it may only take a quick prompt to question alignment to the bigger picture:

Which of our strategic priorities does this link to? 
Is it something new we’ve failed to think of?


Commitment does not necessitate rudeness – but it does ask for integrity, consistency and reasonable boundaries. Like all challenging interactions, a bit of preparation goes a long way. 

For another group I coached last week, this meant the development of a ‘script’ which included three short phrases the senior leadership team agreed to use when communicating new direction with the team. ‘Try new things’ and ‘step up’ (two of the soundbites agreed on by this team) are a lovely example of scripts that are both clear enough to maintain focus, and ambiguous enough to enable ownership and meaning-making by the receiver.

These communication skills aren’t a nice to have – they are a necessary and core component of providing leadership and fostering wider ownership. And ownership, by it’s nature, starts with us. Everytime we seize our agency, take ownership and challenge the ‘way things are done’ by letting go, asking questions and saying no, we lead by example, and free others to do the same. 

Life will always produce too much. Too many things to worry about, too many people to please and too many options to choose from. Dr. Henry Cloud suggests that many of us choose to be disempowered by this, perceiving events as personalised (I am bad), pervasive (everything I do is a disaster) or permanent (nothing will ever change, why bother). Worse, we can make subpar choices that enforce a sense of moral rightness, believing that our loyalty and willingness to take new things on will be rewarded.

OR you can choose to take ownership, and be pragmatic, prepared and empowered. To understand that saying yes to the wrong things robs us of our potential, and makes it impossible for others to reach theirs either.

I know which option I’m choosing this week – and the conversations that I need to have to get there.

As with most things worth talking about, the Stoics said it best. Seneca, in around 60AD wrote “If you really want to escape the things that harass you, what you’re needing is not to be in a different place but to be a different person.”

Works for me.

Alicia McKay