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!

The Virtual Manager

While 2020 wasn’t the year any of us expected, 2021 shows great potential to deliver on many anticipated resets. And we’re ready! Ready to move beyond the pandemic, ready to reset company goals, and ready to feel energized for the year ahead.

Companies are talking to employees, industry experts and business partners to get a sense of what those resets will be. One that is generating a lot of discussion is the work from home setting. Early survey results show more than 90% of employees like this new setting for work…and they want to reset on where they work and how they work. While some companies may continue to work fully virtually, most will reset a new normal that isn’t fully back to where we were in 2019 and won’t fully continue as we are today.

But what will continue is a new role: the virtual manager.

When teams began working from home, we coached managers as boundaries around their role became very blurred and unstructured. Overnight, they were managing around and through personal dynamics.  And they had to learn how to track work dynamics, personal dynamics and emotional distress over a virtual platform.

We wrote about the big shifts (It’s Getting Personal , March 2020). And we quickly saw that most managers were hesitant with them, some managers were tentative about them, and by the end of the year, all managers adjusted to them.

Managers were coached quickly to lead with empathy and understanding in 2020. Now, the expectations of a manager have reset again in 2021, and managers are still learning to manage virtual Productivity, virtual Connectivity and virtual Collaborability.

Here’s why:


While managers still have empathy for dynamics surrounding a work from home setting, there has been a reset on expectations. Many employees worked very consistently through the pandemic; others were more sporadic. The result is managers who are trying to figure out how to allow for flexibility while adding more structure and pressure to deadlines and deliverables.

It means they have to be focused on how they set expectations and clear in how they communicate those expectations. And they will have to balance the pressure that one person’s flexibility puts on another person’s deadline. They will manage some people who come in the office and others who remain at home. They will feel more pressure on their own schedule as they try to adjust to everyone else’s.

We’re helping managers with meeting agendas, difficult conversations and a more structured plan for updates. Everyone is still learning.


Managers worked hard throughout 2020 to connect with virtual employees. It almost doubled the amount of time it takes on their calendars. Most say they never really tracked the hallway chats or drive-by conversations in the office. But they’ve learned to track touchpoints now so that they can balance how often they check in and who they’re checking in with.

The frequency of meetings and checkpoints added some efficiency, but it also diluted some connectivity.  It’s hard to force connection at 10am on Tuesday if your employee is distracted or a little less open at that time. Most managers have tried virtual social time. Some ideas work, and some don’t. There are multiple learnings and adjustments around what employees enjoy and what feels forced.

And for managers, some of this felt critical as companies wanted to stay in touch through uncertainty.  But productivity and expectations are no longer uncertain. 2021 has been reset. So, what will be enough and what will be too much connection? It will be a blended approach in 2021. And most managers hope that some of the in-person and easier 1:1 connection will return.

We’re helping managers manage their time and their priorities. We’re helping them facilitate an open and candid conversation virtually. But everyone is still learning.


This may be the weakest link for the virtual manager. In addition to keeping individuals connected and productive, a good manager takes responsibility for getting the whole team to high productivity. And every manager says it’s harder to do. They can run efficient meetings and report outs, but they miss the group’s ability to really collaborate together. They need the spontaneous thoughts that come when team members talk often and huddle informally around the more complex opportunities.

There are lots of tools, but teams haven’t settled in easily with many of them. In many cases, the challenge is time. To make virtual work productive, managers and employees became very focused on efficiency. And while you can set aside 30 minutes to get a team up to speed, you can’t force out of the box thinking into a short meeting. When you try to replicate a longer whiteboard session, you hit Zoom fatigue with participants.

We’re helping managers’ rethink the format that they can’t replicate. We’re leveraging ways to create small discussions in large groups and prework before brain work.

And…everyone is still learning.


It’s a dynamic and evolving skill, and our coaching is evolving right with it. We see commonalities in challenges and different approaches to good practices. And once companies commit to their virtual work strategy, we’ll know how expanded a future manager’s skills need to be. For now, we’ve created a format that combines real-time coaching with small group discussion. Our Virtual Manager coaching circles run for six weeks and support real-time issues with tangible tools and solutions. It allows a manager to learn fast from shared group experiences. It drives discussion, camaraderie….and a little fun!

If you’d like a little support during the 2021 resets, reserve your spot in your Virtual Manager cohort here.

And as always, we’re here when you need us!

Sally Williamson

The Stories Behind a Purpose with CeCe Morken

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These days, we’re all exhausted. And it’s not just the physical tiredness of managing kids, virtual schooling, shifting work locations in a house, or balancing disruptions as our personal lives and workspace converge. It’s a mental tiredness and fatigue, and the effects are pretty dramatic.

It’s a good thing that companies were already working on body and mind wellness. Wellness support and training has become an integral part of many company’s benefit plans and training initiatives. The added stress and uncertainty of the pandemic has intensified the conversations about mindfulness, meditation, and a company called Headspace.

On this episode of What’s Your Story, Sally’s guest is CeCe Morken, President and CEO of Headspace, and she’s here to share The Stories Behind a Purpose, her experience with how she found herself in this role, and how to manage, inspire, and support a team virtually.

More about CeCe Morken

CeCe Morken serves as President and Chief Operating Officer of Headspace. She is a highly accomplished technology industry executive with 35 years of experience building and growing organizations, from start-ups to global, publicly traded companies.

CeCe joined Headspace after 13 years at Intuit, where she led multiple business units. She served as Executive Vice President and General Manager of the Strategic Partner Group, responsible for the accountant, financial institution, and enterprise platform business generating $700M in annual revenue — in addition to leading both the Corporate/Government Affairs and Corporate Responsibility functions for the company. Morken was also responsible for building strategic partnerships between Intuit and financial institutions, government and educational entities, and enterprise platforms, and also responsible for expanding global engagements, which doubled the velocity of contracts in the target countries of the UK, Australia, Canada, and France.

Before serving in this capacity, Morken led Intuit Financials Services (IFS). She led this business through a technology and business model transformation that moved the business to the number one ranking in share and product design across online and mobile platforms, leading the industry in open platform designs. Subsequently, CeCe led the strategic decision to divest the business and close the sale to the private equity firm Thoma Bravo in August of 2013.

Morken is a graduate of North Dakota State University, with majors in Economics and Business Administration, and attended the University of Chicago Booth’s executive development program. Morken currently serves on the Boards of GENPACT and NDSU College of Business.

Morken has also been recognized as one of The Most Powerful Women in Accounting (2017), National Diversity and Leadership Most Powerful Women in Technology (2017 and 2019), and has received the Intuit CEO Leadership Award in 2011, 2014, and 2017, and the Bill Campbell Coaches Award in 2018.

Show Notes

  • Headspace: Improve health and wellness of the world. This organization helps people build healthy routines through mindfulness in an app.
    • 46% of people over the age of 18 will have a diagnosable mental health issue
    • 60% of those are untreated
  • Purpose of Headspace: Corporate social responsibility and working in service for the greater good.
    • What is the impact of mindfulness thinking?
    • How mindfulness has changed the workplace
  • Study by Headspace:
    • 65% of employees report that most of the stress they feel is from work
    • 42% state that work/life balance is the greatest source of stress
    • 45% of those lose 2 hours a day because of stress
  • There has been an increase of CEO’s listing mental health and mindfulness as a priority in the workplace. With the emphasis on this from other companies there are positive results and improvement.
    • Employers need to enable people to bring their whole selves to work. Virtual environment has mad that difficult
  • The Headspace work environment is one to model. They offer the following:
    • Meeting breaks
    • No meeting days
    • Every other Friday off
  • Headspace offers support programs for companies and shares their best practices with their employees
    • Offer flexibility for the caregivers in the family to prevent losing women in the workplace
  • Mindfulness isn’t about taking more time, it’s about being present. It’s not about time, it’s about frequency. Being purposeful with your time.
  • Headspace got big names like Sesame Street, John Legend, and other celebrities involved.
  • Headspace Outreach
    • Working with Governor Cuomo’s office giving all New Yorkers access to their app for free
    • Worked with other states hit hard, early on, by the pandemic
    • Made their app free to every unemployed person, all health care providers, and educators
  • Headspace provides content like: music, stories, sleep casts, etc. All offerings are backed by science and clinical studies.
  • Headspace worked with Sesame Street with the goal of helping young minds develop healthy habits.
  • Hundreds of thousands have taken advantage of their app.
  • CeCe shared a Storytelling meditation clip from the Headspace app on Wisdom: Mind, Body, Speech
    • The clip covered intention, mindfulness, voice and body of speech.
  • How to manage, inspire and support a team virtually:
    • Best practices for management:
      • Don’t just ask “how are you?” ask “really…how are you?”
      • Start the conversation with their development, not just the business outcome
      • Be a good role model – take breaks, set up healthy boundaries
      • Ensure that you’ve got clarity of common purpose and do “less” better
      • Remind people why you are there and what you are focused on.
      • Speed – don’t wait for normal – make a difference and take advantage of the situation and lean in more.
      • How you spend your time is important, pick your career for the right reason.
      • Find purpose in your work.
      • Do something that makes your heart beat faster every day.

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