By Oga Chan, Founder of North AdaptiveWhy it happens
Why do kind, capable leaders avoid hard conversations? Often because they've seen one go badly, and it left a mark. That can happen, but it isn't the rule. Being assertive at the right level gets you clearer results, saves time and gives your team clarity. Push too hard without empathy, though, and you get mistrust, fear and people avoiding you.
Leadership is full of pairs like this: two values that pull against each other, and you need both. You need to be assertive. You also need to be empathetic. Barry Johnson calls this polarity management. Richard Bolden and colleagues call it the leadership paradox. Either way, the answer isn't to pick a side. It's to hold both, and notice which one you lean on so much that you are no longer effective. For many kind leaders, that lean comes from a hidden commitment, such as wanting to stay liked.
A story from my work
Daniel* reports to demanding stakeholders, and he tended to say yes to every request, however many plates he was already spinning. One week, he pushed back on a stakeholder meeting that wasn't a good use of time for either of them. Later that day, one of his team said he looked relaxed, unlike most Tuesdays, when stakeholder meetings left him so tense that his staff were afraid to approach him. He hadn't realised his lack of assertiveness was spilling over onto his team. Saying no didn't just protect his time. It set a boundary on what got passed down to them. “What shocked me even more,” he told me, “was that my stakeholders appreciated my pushback. It gave them clarity on what I was thinking.”
*Name and some details changed.
What to try this week
What's one small, safe step you could take this week to practise being assertive? Small and safe matters. If it goes wrong, nothing breaks. If it goes right, it proves you can stay yourself and still be assertive.
Try this. Pick one request this week that you'd normally say yes to without thinking. Decline it, or ask a clarifying question instead. Prepare your one sentence in advance. Afterwards, jot down what actually happened, next to what you feared would happen. Most people find the gap surprising.
It's like building a new muscle in unfamiliar territory: a little at a time, safely.
How I can help
In one-to-one coaching, I help you find the hidden commitment behind your hesitation to be assertive, then design experiments that stretch you without putting your relationships at risk.
If it's an issue across a whole team, I run leadership sessions where we map the upsides and downsides of values that pull against each other, like assertiveness and empathy. Your team leaves with a shared way to spot when one is tipping too far, before it does too much damage, and share the responsibility to manage that balance.
I work with business owners and leadership teams across Aberdeen, Aberdeenshire, the Highlands and Islands, in-person or online.