How to Question a Difficult Boss
November 8, 2018
How do you question someone who is in a position of power? What if that person is not only powerful, but also has a personality, set of values, or way of working that is significantly different from your own?
The recent exchange and fallout between CNN’s Jim Acosta and President Donald Trump gave the world a powerful snapshot of how badly inquiry can sometimes go. At their worst, questions are divisive, unconstructive and harmful to relational capital.
But when inquiry goes well? The benefits are staggering. When those in positions of authority are asked good questions, and when they respond well to those questions, powerful things occur:
- Knowledge is shared and the door to diversity of thought is opened;
- Trust between different levels of organisational hierarchy is nurtured; and
- Hasty decisions can be refined, enabling business to be executed more strategically.
The founder of Dell Technologies, Michael Dell, sums up the value of questions well: “Asking lots of questions opens doors to new ideas, which ultimately contributes to your competitive edge.”
It is one thing to reap the many benefits of inquiry when working in a supportive environment. It is much more challenging to question those in positions of power who you feel are not on your side.
Here, therefore, are three tips to help you question a boss who you find challenging to work with. (In fact, these tips will also help you in meetings with colleagues and external stakeholders that feel more like adversaries than collaborators.)
1. Initiate with care
No one likes feeling threatened, and cynicism is easier to come by than humble openness. To help your boss receive your question and give you a constructive answer, the way you begin is key.
Consider the way that Jim Acosta began his question to President Trump, “I wanted to challenge you on one of the statements you made in the tail end of the [midterm] campaign…”. If the questioner begins by saying they want to ‘challenge’, then the context they create for all parties involved is one coloured by opposition.
Instead, set a different scene for your question by asking for permission. ‘Can I ask you a question?’ is an invitation that implicitly acknowledges respect for the other party and sets a more collaborative tone.
2. Check your source
We have all been in meetings were ‘questions’ were asked that were not really questions. The speaker may ask something which is a sentence ending with a question mark but is really a thinly veiled opportunity for them to assert their own perspective, score political points, or elevate themselves over another speaker. ‘Thank you for your presentation John, but don’t you think that…?’ and ‘Don’t you think it’s time we moved on?’ are two such ‘questions’. The temptation to ask these kinds of ‘questions’ is very common and normal, but such veiled assertions are ineffective and unable to do the sharing and refining work of which the best, authentic, questions are capable.
To set yourself and your boss up for success, take a moment to consider the true source of your question. Where is your question springing from? Why does your question matter? What good work do you hope your question will do? And what is the ultimate target of your question? If you find that your question is grounded in authentic curiosity or concern for the welfare of a project, colleague or the organisation as a whole, you can proceed with greater confidence. If you find that your question comes from a desire to score points, prove someone wrong, or make your voice heard, then, congratulations, you are human, but your question may need to be refined before it can do its best work.
3. Give, and take, time
If you need to question someone who you don’t tend to see eye to eye with there will likely be moments where tempers flare. In the recent Acosta/Trump exchange this happened almost immediately. Before Mr. Acosta finished asking his first question, President Trump uttered, ‘Here we go…Let’s go…Let’s go…’ as if inviting a fight.
When tempers begin to flare, it is important that time is given for each person’s perspective to be heard. Throughout their exchange, Acosta and Trump hardly let each other finish a sentence, and this only serves to inflame the heated disagreement. It is much more positive to slow down, ask your question with care, and then leave space for the other person to give their full response. This approach makes the person you are questioning much more likely to feel that their perspective has been heard. In turn, they will be more likely to consider your views as well.
Forming and posing the kinds of really effective questions that have the power to cut through even the most divisive meetings is a skill that can be learned, but it takes practice. These three points are a start, and just implementing them can significantly improve your ability to ask good questions in difficult situations. To continue growing your practice of inquiry at work, check out Philosophy at Work’s Think Laterally workshop.