In Part 1, I discussed handling challenging questions. As an example, I used Boaz Weinstein’s interview with Investor’s Chronicle. This week, let’s flip the script and explore how to ask challenging questions effectively.

Challenges of Asking Questions

We often assist our asset management clients in questioning company leaders to uncover specific insights about potential investments. They face several challenges, such as:

• Investor relations departments sticking to prepared talking points.
• Some information is restricted for good reason (and by law) but this can be used as a shield.
• Management being suspicious of investors’ objectives.

We emphasise prioritising the information you seek. It’s more effective to ask five questions on the same topic and gain useful insights than to ask five different questions that elicit pre-prepared responses. Keep your questions simple and to-the-point.

Focus on a Single Issue

A good example is last week’s Prime Minister’s Questions in the UK. Opposition leader Kemi Badenoch had previously been criticised for asking about too many topics, which diluted the impact of her questions and allowed the Prime Minister to deflect without follow-up challenges. Last week, Badenoch focused on an immigration case, repeatedly questioning the government’s stance. This should have been a more effective approach. However, it was agreed by most commentators that her questioning failed to hit the mark. Why?

Badenoch asked about the immigration case in her first question and asked if the government would appeal agains the ruling. Prime Minister Keir Starmer agreed that the ruling was wrong and this took the sting out the attack. In fact, Starmer had not actually answered the specific point she was asking about. Would the government appeal against the court’s ruling?

Keep It Simple

Badenoch pressed Starmer on this but, crucially, used a really complex question. This made the example hard to understand for a general audience and easy for Starmer to avoid the specific point he didn’t want to address. ‘Will you appeal the ruling, yes or no?’ would have been a better way to show he was avoiding the question.

As it was, Starmer managed to turn the attack on Badenoch saying that he had agreed with her and she was jut following a script rather than listening. She then had to defend her questions which meant she was in the hot seat instead of Starmer.

Conclusion

The learning point is to stay focused in your questioning and when you want a specific answer, keep your questions simple.