#1 How to challenge others (when you don’t feel like you can….)

There have been many times where I’ve been asked to (or expected to) share my opinion, challenge, or give feedback on a work matter but something stops me from being able to do so.

Sometimes this was because other people in the meeting were louder and more confident than me which made me doubt the thoughts that I did have. Sometimes it was because I was intimidated by the people in the room with me — they went to better universities or had previously worked in fancy companies and so I believed they must be smarter than me and will naturally have covered all obvious feedback. Often, it was because I didn’t know what I thought; I wasn’t an expert on the topic so didn’t have a strong opinion or did not feel qualified to have one. And finally, sometimes, it was because I didn’t want to seem rude. I didn’t want to make a fuss or be angry or confrontational. The result? I was not challenging others as much as I should be.

Challenging others and providing feedback is an important part of professional life. It is important to help others make the right decisions, to help them consider an alternative perspective, or to make sure that the work being done is in alignment with the company goals and is achievable. It’s definitely easiest to challenge when you’re naturally in a position of power (i.e. giving feedback to someone you line manage) but I’ve found that it can be an uncomfortable experience when doing so with peers or those in more senior positions.

Here are some of my learnings on how to add value or challenge when you’re in the following situations:

1) When you really don’t know what you think

It’s much easier to challenge when you’re an expert on the topic but in a fast-moving company, you will not have time to become an expert on everything before you feel you have earned the right or the responsibility to share your opinion.

When you don’t really have a strong opinion, you can add value to the discussion or challenge by asking some really good questions such as the below. Don't assume that others will ask these. Some of the questions I like are:

• What is the objective? How does this help your objective?
• How will you measure if your activity is successful?
• What is the goal of the activity and does it change the baseline of the business?
• Why could it fail?
• What do we have to stop doing in order to deliver this?

Every question doesn’t need to be a game-changer, but the act of asking helps expose weaknesses or strengths in the activity which is really helpful.

Secondly, it is perfectly fine to say that you need time to think and that you will share your thoughts tomorrow. We all work in different ways and if you are like me, you will need time to process, talk to others and read the details at least a few times before you figure out what you do think. It's important to recognize that you work in this way and to ask for the time and the space to help you form your opinion.

2) When you think others are smarter or more “ qualified” to give feedback

Classic imposter syndrome. You feel others are more qualified to share their opinions and therefore you feel you should not share yours. The reality is you would not have been asked your opinion if others did not believe it was worth hearing.

If this is holding you back, then I suggest starting by listing the 3 areas that you do believe you are an expert in.

What do you feel like an expert in? For me, this was:

• Our operations and the supply side of the business
• Our company history & culture
• How to lead teams

Once I had my list, I felt much clearer about the types of feedback I could provide and how to go about doing that. It helped a lot with the brain freeze that I sometimes experienced when asked on the spot “ what do you think?” and found that it gave me a structure as to how to organize my feedback. I stopped worrying that I didn’t ask fancy questions about finance or engineering or marketing, because I already knew that these were not my expert areas. Instead, I would review the idea and think about the questions or feedback I had in light of my “expert areas”; Would this work with our current operations? Do we have the team to do it? How would we motivate them? Have we tried this before and did it work?

Do not assume that others will even think about these areas, let alone be an expert in them.

3) When you don’t want to seem rude

Reframe what you think “challenging” actually looks and sounds like. When you think about people who challenge a lot — what do you imagine?

What I learned is that “challenging” doesn’t mean criticizing someone else’s work, giving negative feedback, or pointing out what is wrong. It doesn’t have to be in a loud, critical, or angry tone.

It can be:

• Asking questions like the ones above.
• It could be asking for more information
• Sharing your concerns calmly because you care about the outcome of the activity and want it to succeed
• Asking the thought process behind an idea

All of this can be done calmly, kindly, and whilst smiling 😊 Challenging does not mean criticizing.

So in summary, in a fast-moving organization, we all have the responsibility and the right to challenge and share our opinion. Don’t let your demons hold you back from doing so.