Leading a Company Strategy Shift | How to Not Freak Out Your Teams

Shelby Stewart
Jun 26, 2018 · 7 min read

Panel Hosted by Women in Product and Thumbtack

When you work in product, things can change rapidly, and often that can cause stress and panic for those working around you. So how can you manage that while leading a successful strategy shift? Luckily some wise leaders in product offered great advice.

So first things first — how do you decide when to pivot and shift your strategy? There can be many reasons, such as it came from the top-down, but the panel agreed that often it comes from data, your market, and your customers. Sometimes something changes or sometimes you realize something that you didn’t before.

Now that you’ve decided that it’s important to make a change to your strategy, given new information, how do you go about socializing it to others?

  1. Practice your presentations and start using deliberate words that your customers do. Preemptively start bringing up this language with stakeholders and others in meetings, so you can gut check your new strategy. If you start to see positive reactions, then formalize the plan by talking to your team and getting it on the roadmap.
  2. Get your stakeholders aligned and have one-on-one conversations with people in leadership. It might always be good to set up cross-functional groups to review the data and present it to the team and stakeholders in actionable ways.

After you’ve told others about this strategy shift, how do you deal with any team push back on the new strategy?

  1. Make sure you’re constantly creating a positive culture of change. Change happens, and it’s exciting and cool! If you help cultivate that thinking, your team will be much less freaked out by pivots.
  2. People need to understand why change is happening, so they can decide if it makes sense. Present the data, and then commit and move forward.
  3. Try to relate everything back to your North Star or company’s mission, because the “why” will remain constant; instead, the only thing that is changing is the “how.”
  4. Celebrate the little wins and tie everything back to the larger narrative.

Sometimes there’s many people involved in your team, how do you find the appropriate amount of people to involve in strategy and decision-making?

  1. Include the right stakeholders early, so they can buy-in and advocate for the shift.
  2. Make sure you share your ideas early, but not too early. Half-baked ideas can turn people off.
  3. You don’t need to involve everyone in decision-making, but make sure that you always share how you’re making decisions, because people appreciate transparency.
  4. Sometimes it’s good to create a quick mock-up, because it gives your team an idea and something to react to. This allows a team to team to explore first and brainstorm and then commit to decisions later.

Change can be hard, so how can you help your team cope?

  1. Always recognize that change can be hard and empathize, because it’s important to keep up morale. People need repetition, so always repeat the why.
  2. Try to remove ambiguity — sometimes people don’t want to brainstorm after they’ve just made a major pivot and instead they need a leader who can provide guidance. It’s okay to occasionally tell your team what to do with specific deadlines, so you can give them structure. Later, when things have calmed down, you can think about brainstorming.

How do you deal with opinionated stakeholders if they disagree with your pivot?

  1. Be up front. If you don’t agree with their idea, tell them, but always tell them why. Contextualize your decision with data. Ask them why they want whatever they are asking for and how you can make that happen?

How do you make your teams feel fast/productive during shifts?

  1. Communicate that there will be highs and lows, and that you won’t always be at 100%. There are different types of work, and it’s okay to give your team time and space to do research.

And after all that, what can still go wrong?

  1. Sometimes, when you focus too much on one thing, you forget other parts of your business. So make sure that you don’t narrow your focus too much.
  2. Always think long term with a broad view, instead of short term.
  3. Change is hard for customers, so set expectations for your team and leadership. The initial strategy launch might be bumpy for customers if it’s a big change, but eventually customers get used to it.
  4. Get feedback from everyone and have others point out to you what could go wrong, so you can communicate mitigation plans.

Closing Thoughts:

  1. Make sure the data supports your decisions, get stakeholders on board, present your thoughts clearly and frequently.
  2. Over-communicate — never assume that your team just knows.
  3. It’s fun to lead, so don’t shy away from it.
  4. Embrace change in your personal and professional life, because you’ll be happier and more successful.

Speaker Bios:

Yue Zhao, Group Product Manager, Thumbtack

Yue is the first PM at Thumbtack. She manages the pro growth, storefront and productivity teams and has grown Thumbtack to more than 250,000 monthly paying pros. Formerly co-founder of a wine ecommerce startup.

Ana Grace, Senior Director of Product, Walmart eCommerce

Ana started her career in 1994 at a small internet service provider, where she was the head of marketing (and 4th employee). She remembers when she had to connect a 14.4k modem to the early websites of that time, as an early evangelist for the internet revolution. As the internet evolved, she founded an early web development company and then a web marketing company. Over her career, Ana has held product roles at Best Buy, GoDaddy, and and now oversees end to end customer experience for the Walmart.com website and apps.

Yana Welinder, Senior Product Manager at IFTTT

Yana leads user engagement at IFTTT, which connects over 600 different services and devices to provide seamless integrations to millions of users.

She is passionate about building products that solve core needs and designing the most simple user experiences. Most recently, Yana worked on disrupting manufacturing with digital production at Carbon and tackled free knowledge creation on Wikipedia. At Wikimedia, she led a cross-functional strategy team of leaders from the product, design, and fundraising teams to synthesize internal data and 100+ academic papers on Wikipedia readership and provide strategic advice to the CEO and executive team.

Before finding her calling in product, Yana was a technology lawyer and a law professor focusing on how to align technology with users’ expectations. As a tech policy thought leader, she was invited to speak at the White House, the UN Internet Governance Forum, Stanford, Yale, and NYU, and published pieces in the New York Times, the Harvard Journal of Law & Tech, and a chapter in the Cambridge Handbook of Consumer Privacy.

Cynthia Taylor, Head of Product at dotloop.

Cynthia leads the product management, UX design, and product analytics teams at dotloop, a Zillow Group business that offers an end to end solution for managing real estate transactions. Previously, Cynthia held product roles at Amazon Web Services and Coupa Software.

Christine Lee, Director of Product at Hired

Christine will moderate the panel. She is a co-founder of Women in Product and leads WIP’s Peer Mentoring Circles program. She currently leads the teams building out the candidate experience and internal tools at Hired, a marketplace for connecting tech talent to top global companies. Previously she worked on consumer and enterprise solutions at Twitter, Intuit, and two CRM companies that were both acquired by Oracle.

This event is brought to you by Women in Product and Thumbtack.

About Thumbtack:

Powering the businesses of hundreds of thousands of local professionals per quarter, Thumbtack is one of the largest local services companies in the U.S., offering nearly 1,000 categories, with a working professional in every county in the U.S. Thumbtack helps customers complete millions of jobs — from plumbing, to catering, to personal training to math tutoring. Founded in 2008 and headquartered in San Francisco, Thumbtack is backed by Sequoia Capital, Google Capital, Tiger Global Management, Javelin Investment Partners and Baillie Gifford. For more information, visit www.thumbtack.com.

Women in Product is a non-profit organization dedicated to increasing diversity and inclusion in product management. Founded in 2016 by senior women product leaders in Silicon Valley, Women in Product’s mission is to educate, empower, and create a global community of women product managers to build impactful products at scale. WIP now has nearly 9000 members around the world.

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Women In Product Blogs

Women In Product is a 501(c)(3) non-profit organization dedicated to providing women with equal access and representation in product management careers at all levels. www.womenpm.org

Shelby Stewart

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Women In Product Blogs

Women In Product is a 501(c)(3) non-profit organization dedicated to providing women with equal access and representation in product management careers at all levels. www.womenpm.org