Challenging the boss is an intimidating leadership practice but you can’t shirk it when you have integrity and your boss is getting it wrong. Take it from me: several years ago when I worked on humanitarian responses to ISIS’s violence, my boss deleted a very important line item from a proposed budget — our security personnel. Obviously, I had a lot of understanding and challenging to do.
When you’re touching delicate power dynamics and know advocating for yourself or your team might not go well, the best way forward is with clarity and compassion.
When you know there’s a big challenge coming, the first thing to do is prepare thoroughly. Ask questions, get perspective, consider your argument, anticipate responses, and think through the solutions you want. Don’t skimp on this step – the more important the decision or emotionally charged your response, the more time you’ll need.
Preparation is important for leaders who are either scared or too excited to challenge their boss. Challenging your boss isn't an opportunity to check a box with weak resistance nor is it an opportunity to delight in besting someone with power over you. Do whatever emotional work you need to do to find the center in your approach. The importance of tone and body language is undeniable because whatever emotions you feel – and challenging those with power over us elicits feelings from even the hardiest of us – will be communicated along with your reasoning.
When you feel good and ready, find the right time and place. What will put you both in the most open-minded head space? For my boss, privately and after lunch. Here’s how my pitch went:
I think we need to preserve the security personnel budget. [I disagree.] Having worked in similar agencies, best practice is having full-time local security; they’ve kept me safe in the past when there was a bomb threat and a road raid. [Establish credibility, use reason and stories.] While it’ll save us money at first, I will have to take on that work and it’ll take time from the fundraising goals we set. [Anticipate reasoning and show where your interests meet.] Could we try offering a contract for 6 months and reassess if we find it was not a good investment? [Offer solution.]
I sought clarification and was genuinely open to questions because I knew he had access to information I didn’t. He told me we had security personnel at the global team; I asked how much of their time we’d be able to have. He asked me more about my previous experiences, telling me while he was in management before, it was his first time in the humanitarian context. We talked about other possible solutions like hiring a part time local security consultant.
I knew to leave when the questions dried up and it was obvious he was still on the fence. He had new information to metabolize and there wasn’t anything more I could do then. I followed up with a gratitude email highlighting our main discussion points – it was important to document my disagreement when the liability was so high. Luckily, my boss agreed to a 6 month contract which we renewed.
If he had said no, I would have had a decision: accepting it or deciding whether it was important enough to take additional risk. I’ll share next week on how to tactfully “go over your boss’s head” but for now, we can take our happy ending.
To all my friends preparing to disagree with the powerful people in your life – I wish you luck and groundedness.