Helping Tech to Talk Exec with Mac Smith

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From a distance, you could assume that product creation and innovation is easy because it seems to happen quickly. But you’d be wrong. It actually requires an army of technologists and engineers to keep innovation moving and to deliver products in a speedy fashion. And they aren’t alone. Long before a product reaches a build phase, there are multiple steps to analyze a market, identify a need and propose a product against a market opportunity.

Sometimes there can be a communication conflict between senior leaders and technical teams, and often, the outcome is a lack of understanding and buy-in. It’s why one of the key development needs amongst technology teams is learning to communicate with an executive audience.

On this episode of What’s Your Story, Sally is joined by Mac Smith, who leads Cross Portfolio Research for Search & Assistant, at Google. And he’s going to share his experience with why communication conflicts happen, and how they can be improved.

More about Mac Smith

Mac is the Head of Cross Portfolio Research for Search & Assistant at Google. He leads a 25 researcher organization on research programs that bridge Google Search & Assistant product lines. The team combines product support with cross portfolio programs and processes that increase the overall speed and quality of a 100 person research organization. Before this role, he was the Head of User Research for the Core Search Product, and has also previously led four other research teams for  companies such as Microsoft. 

Show Notes

  • Is there a struggle between executive teams and tech teams?
    • Much of the content struggles to connect at the right altitude to connect with the executive teams.
    • For tech teams who are thinking about how a particular product would work, much of the content in the area of comfort lies around their expertise:
      • The how
      • Data
      • Risks
      • Blockers – etc
  • Try starting with the main point instead of throwing details.
    • The experts struggle envisioning not having all the details to make a decision.
  • The challenge has always been there are repeats on different scales. What has changed as they increase scale is the amount of time the execs have, as well as the complexity they are dealing with has grown exponentially.
    • Perspective difference hasn’t changed – as the organizations have grown, the amount of time you have to make that decision has changed.
    • In smaller scale companies, you have more of an opportunity to work with those decision makers. As the company grows, it becomes more structured and you have fewer opportunities to make those connections.
    • Most of the leadership has spent a considerable amount of time as product engineers prior to becoming executives in tech.
    • It’s important to understand the complexity of systems that run your business so you can make decisions that bridge business, experience and technology.
  • The challenge is many of the engineers have never been in the executive position.
    • From the executive perspective: the aperture of their view, the connection, and the time have all changed – that is the biggest perspective.
    • Executive teams need to come in the door and think about what decision they will make that day.
    • Leaders connect dots. Looking at something a moment in time vs something over time.
  • For researchers there are two parts to the job:
    • 1. The craft of collecting information.
    • 2. The role of being an advisor and a steward of that information.
    • If you are advising or influencing a leader your job does not stop upon delivery of the information, you also need to help/guide that person (the executive) to make a decision.
  • The need for people to have effective communication in their roles has gotten greater.
    • Growth makes communication more challenging.
    • In the early stages of a company, you see more expert to expert conversation.
    • When the audience grows you are no longer having those expert-to-expert conversations. Growth requires you to evaluate how you communicate.
  • How does your expertise connect to the bigger picture, and can you understand the perspective of that executive to help them make that decision or fill in a gap for them?
    • What is the consequence of not being understood?
      • You don’t get what you want. You need to connect it to what the executive wants. If you give me this, you will get this.
  • What is the biggest consequence for not being an effective communicator?
    • Most executives see the company as one large team and they want that team to be successful.
    • If they don’t feel the idea is effectively being communicated, they will send people away and tell them to come back with more research.
    • The communicator must understand what is needed by the executive.
    • Time loss is the biggest challenge.
  • What are the common mistakes that happen over and over again?
    • Presenter starts the conversation from their perspective and misses context completely.
    • The takeaway is buried at the end of the conversation.
    • Presenter is not prepared for the drill down by the executives. Presenter must realize the executives want them to be successful and ask questions attempting to help. They are essentially asking the presenter to give them a reason to change or do something. In this scenario, tech experts miss an opportunity to connect with exec staff because they feel tested.
  • Most technologists want to be better communicators and the biggest challenge they face include being anxious or unsure about effective communication.
    • Tech groups are phenomenal learners, they work hard to make it fit and make it work.
  • How to improve skills as an effective communicator:
    • Start at the end, not from your perspective. Start with the end goal for the audience.
    • Encourage people to prototype their results that they need to get to and show to others. Modify based on their feedback to show the end that you’re going to hit.
  • Do stories have a place in technology?
    • Facts and data are not memorable – add a layer of storytelling to that data. It helps others to understand what you are trying to accomplish and connect to broader business perspective.
    • Set out the board context and framework – here is the what and how of this story, and then illustrate that with concrete stories. When you marry those two together- it takes a complex space with conflicting information and makes it very concrete and relatable.
  • If you learn to communicate well, the chances of you becoming one of the executives becomes significantly higher in terms of probability and speed at getting there.

Like what you hear? Hear more episodes like this on the What’s Your Story podcast page!

Meetings Going Nowhere

Has it really been eight months since we shifted to a different way of working?  Somehow…it has!   In fact, it’s been long enough that email tags have shifted from “working from home” to “back at work,” “in and out of the office” and “still at home.”

We’ve talked to people through the different iterations of virtual work, and some interesting trends have emerged around how people work and communicate with each other.

In March, the early response we heard was: “This really works!” “This is great.” “We got this.” “We’re much more effective than we thought we would be.”

At the time, we assumed virtual work was going well because people knew the work they needed to do.  Big initiatives were already in place for 2020.  Most people were in a phase of execution, and once home, they focused on the things they had to do.

Fast forward six months, and the insights have shifted significantly.  Now we hear:

  • “This is really hard to do.”
  • “It’s impossible to get the input you need.”
  • “I feel like I’m missing direction.”
  • “I’m so sick of working alone.”

People hear about others going back to work and seem envious. They say they want to go back to the office.  I think they really want to go back to working with each other. Because one consistent theme we’re heard all along is: virtual communication is harder.

People say:

  • “There’s just no response when you lead a meeting.”
  • “I can’t get people to participate.”
  • “It takes twice as long to get a decision.”
  • “I’m always misunderstood.”

And it’s why we’ve dubbed this a trend: meetings going nowhere.

Virtual meetings aren’t as effective as they need to be.  In fact, they seem a little chaotic when you ask people what’s going wrong.

  • “There are too many people talking.”
  • “Agendas aren’t clear.”
  • “No one seems sure what the point of the meeting is.”
  • “There are too many people in the meeting.”
  • “No one seems to be in charge.”

A virtual meeting is different than an in-person meeting.  It can be run effectively, but it takes a lot more work to get it organized.  And even though it’s been eight months, few people have built a skill set for leading virtual meetings well. They’re relying on skills they’ve used for years, and from a listener’s perspective, they don’t translate well.

Here’s the root cause: while the “work from home” setting made everything about communication feel more impromptu and casual, it’s actually the opposite. An effective virtual meeting requires more structure to keep a group focused and on task. The discussion itself may be informal, but it takes work to get a group involved.


Here are a few of the differences that we’re helping managers and leaders consider.


This is the hardest format to transfer to a virtual setting.  Hard to believe, because most people love these meetings! They start with a few concepts and quickly build to some great ideas.  It’s the strength of an in-person discussion, and it works because people are 100% focused on being in the room, and they build off of energy and enthusiasm of others. People are very visible, and they work hard to contribute. In fact, they feel a little pressure to show up well.

Virtually, it’s much harder to build on ideas and attach to someone else’s energy. Instead, we tend to stay wedded to our own thought and we just reinforce it when we have an opportunity to speak. And reflection time is dead time in a virtual meeting. If you tell a group to take 10 minutes to write down their thoughts, they’re more likely to take ten minutes and get a snack.

A virtual discussion has to have guardrails and direction to be productive. A virtual group does better with choices of concepts and focused work on supporting a recommendation for a choice versus trying to come up with the broader concepts.

We learned this ourselves as we transitioned to virtual workshops. We gave groups one of  our standard exercises and quickly saw they did very little with it. When we modified the scope of the exercise to making a choice between options, they were able to collaborate better. They needed defined roles and specific instructions of what to do. Their input was very good, but they got there differently.

The same may be true of your discussion sessions.


Do more of this for virtual meetings. Everyone seems exhausted and overworked, but people miss connection. And it will simplify your discussion if you have people work together prior to the meeting instead of in the meeting.

Plan ahead and assign partners to discuss prework together. It’s a benefit from both perspectives. This makes the large meeting discussion easier on the leader because you have reduced the input by half. And, it ensures everyone feels heard because they shared perspective with a partner prior to the larger meeting.


It’s the routine meetings that people dislike the most. The feedback is lack of structure, lack of direction and just no real takeaways. If you’re leading standing meetings, you owe it to a group to improve the takeaways.

Meetings have become more transactional in a virtual setting, but people still want to feel as if their attendance mattered.  It takes more formality and structure to help it run well.

Our rule of thumb is cover less. Simplicity over complexity. These virtual meetings are a hybrid of conference calls and in-person meetings. There’s still a lot of clunkiness in how we experience each other online. So, keep it simple.

Agree on a flow of an agenda and stick to it in every meeting. A consistent structure makes it easier to follow a meeting and easier to hear what’s being said. Agree on how to participate. It’s like learning a new game. Give everybody the rules, and they’ll get a little better each time you hold a meeting.


Companies may have sent the wrong message about the video early on. It was with the best of intentions because they knew that people were dealing with a lot in their homes. But the camera is a signal of focus. It says, “I’m here and focused on this conversation.”

No camera or darkness around someone’s name, says the person isn’t fully there.

And it changes the very essence of communication: Connection. No matter what your role is in a meeting, turn the video on and be fully there as a communicator.


We aren’t as chaotic as we were eight months ago. We’re working differently and we’ve learned a lot from our experiences. If your company is headed into another six months or more of virtual meetings, then learning to lead a meeting that’s going somewhere will be an important skill in 2021.

If you’d like a little help resetting your annual planning session or your team’s routine  meetings, we can help you transition to an effective virtual model.

Call us when you need us.

Sally Williamson

Helping Tech to Talk Exec

You’ve seen this challenge. It’s in every meeting where strategy connects to implementation. It’s where vision meets tactics. And it’s one of the biggest communication challenges in most companies.

Here’s how it happens:

The leadership team wants to expand a product into a new vertical. They’ve seen the numbers to support market size and they know there’s a window of opportunity. They’ve also been told there’s a “little tweaking” that will need to be done in the product’s application to make it viable in the new vertical. So, the next meeting calls for the engineers to come in and explain what’s involved in “tweaking” or converting the product.

The leadership team is looking for a 15-minute explanation to quantify what needs to be done and how long it will take. Instead, they get the step-by-step details of how it will be done.

In an effort to get out of the details and move toward answers, the leaders jump in with questions and assumptions. It was meant to speed up the discussion, but instead it signals to an engineer that the leaders didn’t understand the information. So, the engineer provides more explanation.

The leaders want the bottom-line. The engineers communicate in process and details. And whether the disconnect goes on for several minutes or more than an hour, it’s frustrating to both the executive listeners and the technical communicator.

As a coach I’ve been asked many times: “Why is communicating to the executive level so hard for engineers and technical teams? After all, they are arguably the smartest people in the company!”

Both points are true. Engineers are some of the smartest people in a company, and communicating with executives is a common challenge. It always has been. But companies are noticing it more because technical input has become more critical as a point of influence and essential to making smart decisions.

So, why is “executive talk” hard?

I’ve coached on both of sides of the table for decades and solved for the challenge when I wrote Leading Executive Conversations. But I wrote the book for all audiences who want to solve for the executives’ perspective…and the tech group is a little unique.

Through the years, I’ve learned that it really comes down to how people think, because how they think impacts how they speak. And engineers think in details, steps and precision. And thank goodness they do! Would you want to drive an automobile that was built from a sketch instead of a blueprint? Can you imagine working on a computer that can do 20 things but can’t connect those things to each other?

Whether process-thinking is innate or developed over time, engineers add the greatest value by bringing precision and detail to vague concepts. It’s no wonder that they communicate in details. To tell a leader that they can build a new capability in eight weeks isn’t how they think. And in fact, they wouldn’t be comfortable with that answer unless someone took them through details of what was planned over those eight weeks. It’s how they think, it’s how they work, and that’s why it’s how they communicate. I describe it as communicating from the bottom up.

Yet most leaders think in the opposite manner. They let go of thinking through details of HOW some time ago. They need the What, and the Why. They start with the big concept and challenge whether the WHY has enough value to pursue. They listen to implementation just enough to buy-in. Most leaders think and communicate from the top-down.

And the disconnect comes when the leader feels impatient working through the HOW to get to WHY and the engineer feels the value isn’t justified unless you communicate detailed steps to prove out the HOW.

But it’s a disconnect that’s solvable because you’re dealing with some of the smartest people in the room! And once we figured out why the challenge exists, we developed a process for solving it. And we’ve found that technical teams can be some of the best students of communication.

To help Tech to talk Exec, we developed a process that is based on key insights and a formulaic outline. We’re prescriptive in defining the executive perspective and building specific examples that illustrate how the outline works against common technical topics.

It’s our storyline formula with two key components: a Message and a Framework. This gives an engineer a blueprint to follow that lifts the altitude of their conversation. The details don’t disappear entirely. But the flow of communication is organized with a top-down approach that starts with what executives value and then leads to the technical steps that can be reduced or expanded based on an executive’s interest.

It’s solving for one of the biggest communication challenges in companies today. And it’s helping technical teams become key influencers at a time when their expertise is essential to smart business decisions.

Do you need help coaching tech to talk exec?  We’d love to share our insights and some great success stories about strengthening the voice and the impact of technical teams.

We’re here when you need us!

Sally Williamson