The Challenge of Leadership: Asking for Help "Product people - Product managers, product designers, UX designers, UX researchers, Business analysts, developers, makers & entrepreneurs November 11 2020 True good product leadership, Interview, product consultant, product leader, product leadership, product management interview, Mind the Product Mind the Product Ltd 1566 Design meeting - Photo by Charles Deluvio on Unsplash Product Management 6.264

The Challenge of Leadership: Asking for Help


As one of the leaders in a company, the buck stops with you. And while this is generally thrilling and also what you signed up for, it can occasionally be the source of headaches as well. Whether you’re the CEO, COO, the Head of Product or leading a business vertical – a particular area that is key to your success is, of course, the Product itself.

If you’re a product leader, then you do at least have a sense of what’s involved in the product function and its improvement. However, if you’re a non-product leader charged with improving your company’s product function, then you have a particularly ambiguous challenge ahead of you. Product Management is a very broad topic that’s somewhat harder to judge from the outside than some other areas in your company.

Of course, no matter what business function you’re leading, sometimes it becomes necessary to seek external support, and asking for help is a common challenge in a leadership position. This can be partly because you’re expected to have answers, partly down to culture biases against asking for help, or partly because the options for leadership support are more limited than more tactical support. Either way, there are very good reasons to seek external support, and ensure the process is seen as adding to the company’s capabilities, and we’ll walk through an overview of how to ensure the process goes smoothly.

The Challenge

Many aspects of a product within a company can be confusing: from a misalignment between the vision and the strategy, to features that are being built and not quite addressing the strategy – it’s hard to know exactly what to do to improve the situation. At this point, an experienced external person can bring a wealth of experience and a capacity to quickly identify the areas that need improvement. In addition, that person will be able to put an execution plan together on the steps and sequencing needed to achieve said improvements.

However, to find such a person, to hire them and to have them work inside the company, can be quite tricky. From experience, the main steps in this process will be something like this:

  1. Finding the person! Where do you start? What are you looking for?
  2. Once you have a lead, how can you ensure that person is the right one for your organisation?
  3. And finally, it will be crucial to engage your team the right way (stakeholders / direct reports) and ensure they understand they are being supported, not replaced.

1. The Search

Taking these points in order, let’s start with looking for that person. The first aspect to figure out is what you are hoping this person will help with. Examples would be:

  • Revise and improve a strategy
  • Audit a product and development organisation and processes
  • Help build a strong product team
  • Build a plan for a beta program and define the recruitment criteria
  • … Or maybe you just need a completely fresh perspective on something? Or everything?

A senior Product leader will typically have done these multiple times, and can help facilitate and run these activities.

Once you know the basics of what you want, it’s time to reach out. This still mostly happens via word-to-mouth, starting with fellow Chief Product Officers, Chief Exec networks, and others. While very senior Product leaders are still low in numbers, your options are getting better and better, and there are an increasing number of people available as external leadership help.

Design meeting - Photo by Charles Deluvio on Unsplash
Design meeting – Photo by Charles Deluvio on Unsplash

This also leads to the second approach, which is to look out for what freelance Product leaders are publishing. This can be highly variable between individuals, but can still help you find people, evaluate their thinking, and see whether this would fit what you’re looking for.

2. The Filter

As you start reaching out and building a list of possible consultants and experts, you will face what might be the hardest part of this process: evaluating the fit of a person with your needs. There are a few things you should do to figure this out, none of which are mutually exclusive, so mix-&-match to suit your preferences and needs. So, in increasing order of complexity:

  • Start by asking for content that this person has online and that you can review (articles, recordings of presentations, podcast episodes, etc.) This will help you understand their thinking, how they see impact and progress, and you can get a first glimpse of whether they are what you’re looking for.
  • Ask them to run you through how they usually start tackling this kind of challenge. A senior product leader will have an approach – even if it’s just key questions to ask – and be able to outline what their first steps would be in working with your team. This kind of quick conversation can often be enough to clarify whether someone has understood the challenge you’re facing, and might even give you early indications that someone is a perfect / terrible fit for your organisation.
  • To get a more in-depth view, you can organise a 2-hour session with the product leader, yourself and maybe one other executive from your organisation. Run through what you want to achieve overall, what you think the current obstacles are, and the person should quiz you to get enough information to have a semi-tailored high-level approach. At this stage, you can generally tell whether the person will be able to help, and whether their approach will fit the operations and culture of your organisation. It should be noted that this will probably be chargeable, since that’s what freelancers’ trade is all about and value will be created. Further, it’s quite time-intensive, so it’s a step to think about carefully.
  • Lastly, as a more advanced due diligence, you can start by engaging the person in an initial piece of work (essentially a prototype, or an MVP). This will be limited in scope and would entail, for example, auditing the Product org + processes by interviewing a number of team members. Several things would come out of this process: a tailored list of recommendations for your organisation, giving you great external feedback, and letting you see the quality and fit of their work. Your team will also have developed an opinion on how well the person understood the problems, and how good the proposed solutions are for the given situation.

At this point, you should be able to decide whether you want a more in-depth engagement with that person, and develop a clearly-articulated goal with them.

3. The Preparation

Bringing in an external person gives many signals to the team – some positive, and some critical – which can be toxic if you leave the situation to their interpretation. To be honest, your team will inevitably have their own interpretation – based on their worries and concerns – no matter what you do, but you do have an opportunity to shape the signals to communicate the right information.

Priming the Team

To make the engagement positive and effective, and to get the most out of it, it’s important that the team understands that this is an investment in their knowledge and skills, and that they can use it as a learning opportunity.

The typical worries that people will bring to this scenario are along the lines of “Oh, I see, the CxO doesn’t trust us since he is getting an expert in”. In all honesty, it might be true that there is some corrective action happening. However, more often the expert might just be there to:

  • Empower the team and accelerate the pace,
  • Improve the cross-functional alignment by drawing on experience that simply isn’t available within the company
  • Or even to just coach the team to progress faster, as an investment in their professional development.

It’s important that this discussion takes place openly, and before the expert joins. This way you can manage expectations, create space for open and honest conversation, and be absolutely clear that this will benefit the team, as well as the company as a whole.

Maximising the Impact

The second aspect is to prepare for a learning phase, which requires the team to be ready to absorb a lot of knowledge and insight as quickly as possible. Some of this will be in the form of explicit instruction & coaching from the external expert, and the team needs to be ready to take that on board.

What’s at least as valuable – and requires more positive engagement from the team – is observing how the expert approaches and solves issues, as this can highlight many behaviours and processes to integrate into the company’s own product development process. This will range from ways to define goals, prioritisation frameworks, or regular rituals focused on the product development process.


Getting help for your company from a senior product leader can be a great contribution to your company – it can be anything from emergency input to a planned investment in team process. The key is to execute it correctly, and align the pieces ahead of time. If done well, you’ll enjoy a crisper roadmap, a more focused execution, and an empowered team driving huge positive outcomes for the company.