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4 Questions New Leaders Should Ask

IDG (parent company for CIO, Computerworld, CSO, Infoworld, ITWorld and  MACWorld) asked what advice I would give new leaders. At the moment, I didn’t think it was going to be that hard. But then they added a constraint. I had to do it in less than 5 minutes. So I shared what I did when […]

Phil McKinney
Phil McKinney
4 min read
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new leaders should ask questions

IDG (parent company for CIO, Computerworld, CSO, Infoworld, ITWorld and  MACWorld) asked what advice I would give new leaders. At the moment, I didn't think it was going to be that hard. But then they added a constraint. I had to do it in less than 5 minutes. So I shared what I did when I took over as CEO at CableLabs, which was creating the 4 questions new leaders should ask to better understand the organization they are joining.

Watch the video on IDG.TV

For those who don't want to watch the video, here is the full transcript, including the questions I would suggest new leaders ask when taking on a new role.

4 Questions New Leaders Should Ask

CONGRATULATIONS!! You just got promoted to a leadership role!!

It’s like the old saying goes — be careful what you wish for!!!

Taking on this new role will challenge you.

Leadership requires a new set of skills to be successful — beyond the skills that made you successful as an individual contributor.

One skill that you will need to apply immediately is your big-picture thinking. You need to quickly grasp and prioritize what needs to be done to make the team and organization successful.

While you may think this action only applies when you are taking over an existing team or organization — trust me — it also applies when your boss is asking you to create a new team.

You don't have the time to lean back and wait for things to reveal themselves. You were put in the role to lead — so lead.

So how do you grasp what is truly going on?

The answer may sound simple — you ask questions.

But not just any questions…questions that will jar loose what is really going on and help you understand the opportunities and challenges you are facing as the new leader.

Over my years of experience in large venture-backed and corporate startups, as the CTO at HP and now the CEO of a company, I’ve honed the four questions that will not only allow you to gather the information you need but that will also communicate to others that you are ready to take on this new leadership role.

Ask these four questions to your key stakeholders, like your boss, your peers, your team members, and any others who will play a role in your success including other executives. This includes questions to ask a CEO.

The first question is ..

1) What are we doing well and that we should keep doing?

Start with a question that asks for positive feedback on what is working.

Why? People tend to be much more comfortable giving feedback on what is going well and it shows that you are looking at the good first – before looking for what is wrong.

This question builds an open dialogue that you can leverage later when you are asking for more honest feedback.

Next, ask …

2) What are we doing that is of no value and should we stop doing it?

This gives the person permission to share the issues that you may need to address at some point. If the person starts rattling off a long list, ask them to prioritize the top three they would suggest you focus on.

.. and now that you’ve warmed them up, ask questions that will elicit unexpected answers  ..

Start with ..

3) So — I’m the “new guy”. What is it YOU most hope I do?

This is a question that will cause the other person to pause — and ponder. I have found that this question causes them to dig deep because of the word “hope” .. hope triggers an emotional response that gets people to offer up something they themselves wouldn’t have been willing to share …

.. and then ask …

4) So again — I’m the “new guy”. What are YOU most afraid I might do?

This is the unexpected question that will cause the person to go “beyond the obvious”  .. “Afraid” is another emotional trigger word that will cause the person to bring up their most private fears/concerns about you as a leader ..

Warning —- This process will test your “active listening” skills…

Don’t react… don't respond … just take notes — and maybe ask a few clarifying questions to make sure you understand their answers.

After asking the questions —- thank them and commit to getting back to them with your thoughts after you’ve completed the rounds.

Collect your notes and look for patterns in the repeated comments, words, and topics for each of the four questions….

The answers to the questions will give you a good understanding of what is working and areas you need to dig deeper on.

Let what is working keep working and focus on the burning issues you heard repeatedly .. especially on the answer that you got from the last question.

Don’t make the mistake most new leaders make by waiting for “permission” before you investigate and address the most pressing issues…

They put you in this leadership role for a reason… start leading!


These questions will not only unlock what people are thinking, but give you a roadmap of what you need to focus on in the near term. What could be better as a new leader? Especially when you create smart questions to ask your CEO.

If you are looking for help in increasing the innovation impact for your organization, see how the team can help.

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Phil McKinney is an innovator, podcaster, author, and speaker. He is the retired CTO of HP. Phil's book, Beyond The Obvious, shares his expertise and lessons learned on innovation and creativity.


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