Preparing for High-Stakes Interviews Part 1: Boaz Weinstein

by | 13 February 2025 | Authority, Communication, Leadership, Q&As

Fielding Tough Questions

We are often asked by clients to help them prepare to deal with tough questions in high-pressure situations. Listening to two completely different interviews over the past couple of weeks has highlighted some key lessons on this topic – not only for those answering the questions, but also for those asking them.

In this post I’ll talk about Boaz Weinstein’s interview with Investors’ Chronicle. This gives us useful insights into the interviewee’s perspective. Next week I’ll talk about how Kemi Badenoch approached Prime Minister’s Questions on 12th February to give insights into the questioner’s perspective.

Activist or Opportunist?

So first to Boaz Weinstein. If you know anything about the UK’s Investment Trust sector you will have come across his name. If not, he’s a hedge fund manager seeking to shake up a beaten-up sector of the investment world. For one side he is an activist hero with investors’ interests at heart, for another he’s a short-term opportunist who is in it for personal gain rather than the good of investors.

Where We Start

When working with our clients, our starting point is to ask them what ‘Typical and Difficult’ questions might come up. If we’d sat down with Boaz Weinstein before this interview and gone through his ‘Typical and Difficult’ question list, we would have predicted most of the questions he faced. These included:

  • Do discounts matter? (For more on the importance of discounts in this context, see this excellent explainer.)
  • What will you do if you win?
  • What will you do if you lose?
  • What next?

The aim when looking at Typical and Difficult questions is to have a response that lands your key message. For the first question, Weinstein did. I won’t go into the details here – explaining how the UK’s investment trust sector works is a longer post for another time. Suffice to say, Weinstein argues that he’s already delivered for investors to the tune of £150 million. It’s a strong answer that reinforces his key message.

Muddying the Waters

In our view things get more difficult as interviewee and interviewer start to pull in different directions. Weinstein wants 90% of the interview to be about discounts and bad management by the current boards. The interviewers want to talk about the future. As a result, the conversation is not as illuminating as we would have liked. Weinstein himself comes across less strongly.

Why Our Solution Works

This is where our ‘Typical and Difficult’ list really delivers. When preparing for a Q&A or interview, we might have a very clear idea of what is most important for the audience. However, the interviewer might have a very different idea. The discipline of the ‘Typical and Difficult’ list makes us do the work on the areas that are less interesting or comfortable for us. By anticipating where an interviewer might go, we can avoid having our strong answer undermined by weaker answers on areas we have prepared for less.

I’d be delighted to hear your thoughts and look forward to speaking about the questioner’s perspective next time.

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