Andrew MacGill shared his insight that he’s gained as the former Pager SVP of Product on handling product-focused bosses and more in great detail. Please enjoy the entire video of his presentation from his Speaker Series event in New York.

The highlights of his presentation are detailed below.

On good Product Leaders

MacGill first discussed the qualities of a good product leader, but then he really broke it down into what it takes to be great at managing product-focused bosses.

  • Gather information from a variety of different stakeholders
  • To carefully balance competing priorities
  • Intuitively assess risk
  • Deeply understand our domain

“We know how this place works, we understand the inner machinations, and we assume that our inherent expertise is enough. Suffice to say, that the leaders that we serve and the leaders that we work with, whether they’re our direct boss, whether they’re the CEO of the company, whether they’re leaders of other parts of the business, we assume that because of that, they should just, quote-unquote listen to us. Our inherent expertise is frequently not enough or effective. 

Our effectiveness as product leaders depends on our ability to sell our ideas, and negotiate with our leadership in the interest of building and growing our teams, building and growing our companies in building in developing and growing our products. If negotiation, and this is a phrase I’ve heard in the past, is nothing more than communicating with results. Then as product leaders, we need to be good at that.”

The first step in managing product-focused bosses is to identify their personality type.

According to MacGill, there are four different personality types.


“So assertive is goal-oriented. They’re decisive and they’re competitive. They care deeply about the bottom line of their companies and, frankly, their own personal bottom line. And they believe that in many ways, time is money. Every wasted minute is a wasted dollar. More often than not, their self-image is linked to how many things they can accomplish in a period of time. They live by the mantra that perfection is the enemy of progress. 

You can spot their animated and confident body language from a mile away. They’ll often lean forward in conversations. They’ll gesture while speaking. Most of all, an assertive wants to be heard. And they do not only want to be heard, but they will struggle to listen to each and every one of you and what you have to say until you’ve heard them. They don’t ask, they tell.”


“In many ways, your classic salesperson. Amiables value personal relationships and they want more than anything to trust the people that they do business with. As long as there’s a free-flowing, continuous exchange of information, amiables will often consider their time well spent.

their goal is to be on great terms with the people that they’re working with. Often this means that amiables don’t make decisions quickly. They will seek out help or the approval of multiple team members. You often find that they ask a lot of personal questions and attempt to get to know you outside of your professional role.”


“Expressives are somewhat of a hybrid between assertive and amiables. Like amiables. expressives want to connect on a personal level. But like assertives, expressives are sure of their beliefs and speak in statements rather than questions. Expressives tend to be people-pleasers, but don’t be fooled. Because expressives have powerful personalities, and they use them to convince others of their strongly held convictions. Expressives are strongly creative, outgoing and spontaneous and rely upon aggressively on their intuition, and my personal experience expressives our textbook entrepreneurs and dreamers.

You can spot them based on their enthusiasm, their colorful personalities. And you’ll find that they often speak just like assertive in declarative statements, rather than using questions. Their goal is to say, ‘I think this’ and they expect you to challenge that. They expect to have a conversation around that. If they’re wrong, they assume you will tell them.”


“Analysts are their own breed. [They’re] are methodical, they’re diligent, and rarely in a rush. Instead, they believe that as long as they are working towards the best result in a thorough and systemic way, time is almost of little consequence. Their self-image is linked to minimizing mistakes. And versus the others, you can be sure that an analyst is listening very intently to what you say. Analysts stick to their deadlines, but they do not make decisions quickly. They care about thoroughly vetting and understanding the options that are before them. And they won’t jump the gun on a decision. They love data. They love facts, and they love figures.

You can spot an analyst through their serious, their direct, their formal approach, their emphasis on facts over emotions, and their inclination to ask questions without making statements.”

The second step for managing a product-focused boss is about building trust.

To build trust with product-focused bosses, you need to worry less about what you have to say, and instead open your ears.

“Whether they’re our peers, whether they’re our direct reports, even better yet our bosses, people want to be understood and accepted. Listening is the cheapest, most effective way to achieve this. By listening, we demonstrate empathy, and we show a sincere desire to better understand. When individuals feel listened to, they tend to listen more themselves and carefully and openly evaluate and clarify their own feelings and thoughts.”

A few tips for doing this:

  • Repeat the last two or three words of what someone just said.
  • Make a mutual statement of understanding by starting a sentence with “it seems like,” “it sounds like,” or “it looks like.”
  • Use your knowledge of the different personality types to tailor your listening.

The third step is about bargaining and persuasion.

This next step for being a great product leader that can properly manage a boss is about empathy.

“When we sell our ideas, our job as a product leader is to persuade our bosses to see what we already inherently know. But more often than not, you won’t be able to directly persuade your boss to see your ideas. After all, our bosses can be overextended, they can be overwhelmed. Some of them can be incompetent. In other words, they’re human. Instead, we need to guide our bosses towards our point of view, while making it feel as if their point of view is our own.”

Tips for persuading your product-focused bosses:

  • Always present three solutions. Demonstrate that there are different implications for each approach.
  • Use a stack rank, rather than priorities, to communicate and collaborate on what’s important.
  • Ask carefully calibrated questions that start with “how” or “what” to point your boss towards solving a problem.
About the speaker
Andrew MacGill Pager, SVP, Product Member

Andrew MacGill has worked in the startup world for more than a decade. He currently serves as the Senior Vice President of Product at Pager, which simplifies the healthcare experience by guiding people to the right care and keeping them on the right path through chat and AI enabled technology. MacGill previously held VP of Product Strategy and VP of Product roles at Rally Health and Spotlite respectively. Before that, he was the Director of Product at PerkSpot.

About the host
Tim Holley Etsy, VP of Product
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