Leading Remote Teams Through Ambiguity

There’s a particular kind of organizational moment that directors and managers know well but rarely talk about directly. Strategy has shifted — or is shifting — and the full picture hasn’t been communicated down yet. The team is executing tasks they can’t fully contextualize. Questions come in that you can’t fully answer. And the performance clock keeps running.

This is leading through ambiguity, and it is arguably the most demanding thing a mid-level leader does. Not because the situation is technically complex, but because the human dynamics are — and because the instincts most leaders have developed for normal operating conditions are exactly the wrong instincts here.

This post is for directors and managers in marketing and revenue functions who need a practical framework for keeping distributed teams executing confidently during periods of organizational change. It draws on what I’ve seen in my own leadership experience, and on research from my leadership training at the University of Tampa, where the intersection of emotional intelligence, psychological safety, and change management became central to how I think about leading teams.

Let me be specific about what I’ve seen happen in practice, including in marketing functions where I’ve worked directly.

A leadership team decides to pivot the content strategy. Or reposition the brand. Or restructure the team around a new channel. The decision is announced in an all-hands. The managers are handed the initiative. And somewhere in the handoff, no one has asked three questions that will determine whether any of this actually works:

When uncertainty arrives, leaders tend to do one of two things. The first is to project false confidence — to communicate as though things are clearer than they are, hoping that certainty from above will prevent anxiety from spreading downward. The second is to go quiet, waiting until there’s more to share before saying anything at all.

Both are understandable. Both are leadership mistakes.

False confidence corrodes trust the moment reality diverges from the message — and on distributed teams, where people have fewer informal signals and water-cooler calibrations to draw from, that divergence tends to surface faster and land harder. Silence, meanwhile, creates the very anxiety it’s meant to prevent. Nature abhors a vacuum, and so do team communication channels: when leaders go quiet, informal channels fill the gap with speculation that is almost always more alarming than the actual situation.

The alternative isn’t perfectly calibrated messaging. It’s honest, rhythmic communication that explicitly names what is known, what isn’t, and what the team should focus on in the meantime.

Managing a HubSpot marketing team through multiple periods of strategic flux taught me something that research has since confirmed: remote teams during change need more communication than co-located teams, not less, and the content of that communication matters differently.

In a physical office, a lot of leadership happens through ambient signals — the tone of a hallway conversation, a visible calendar that shows the leadership team is in back-to-back sessions, the body language of someone who just came out of a difficult meeting. Remote teams have none of that. What they have is what you put in writing and what you say on video. When you go quiet, the ambient channel goes dark completely.

The Deloitte Global Millennial Survey of 2020 found that one in five remote employees did not feel trusted by management – a figure that almost certainly understates the perception problem, since distrust rarely announces itself directly. That perception of untrust, once established, makes honest execution reporting less likely, surfaces problems later than they should appear, and reduces the discretionary effort that separates a team executing tasks from a team actually trying to win.

Establishing trust in a remote environment requires deliberate, repeatable behavior — not a single ‘town hall’ and not a culture slide in an all-hands deck. It requires a communication system.

The goal of a change-period communication system is not to eliminate ambiguity — you can’t, and pretending otherwise damages your credibility. The goal is to give people enough context and enough consistency that they can make good decisions at their level without escalating everything upward or freezing until the picture clears.

The system has three components:

Not a status report. Not a project tracker update. A brief, human-language note that answers: what shifted this week that the team should know about, what hasn’t changed and why that matters, and what the team should prioritize until the next update. This takes fifteen minutes to write and does more for ambient trust than any dashboard ever will.

The key is regularity. It’s fine for the update to say ‘nothing major changed this week, but I know some of you have been wondering about X – here’s where that stands.’ Consistency in format and cadence signals stability even when the content is acknowledging uncertainty.

Ambiguity creates decision paralysis at the individual contributor and manager level. People stop making calls they could reasonably make because they’re not sure if those calls are still valid under the new circumstances. The result is slowdown and upward-delegation of decisions that should never reach the director.

The fix is explicit: define, out loud, in a team meeting, what the team has clear authorization to continue deciding on their own, what requires a check-in before proceeding, and what is currently on hold pending more information. This sounds basic. It is basic. And it is almost never done.

Research on psychological safety is clear that people in organizations regularly self-censor rather than act in ambiguous situations — not because they lack judgment, but because the interpersonal cost of being wrong feels higher than the cost of waiting. Naming permissions explicitly lowers that cost. It says: within these boundaries, your judgment is what we’re counting on.

Most leaders during change are focused on the outbound problem — what do I say, and how do I say it? The inbound problem is harder and more important: am I getting honest signals from the team about what’s actually happening?

On remote teams, signals travel through a smaller number of channels. People are less likely to raise concerns in writing than they would verbally. They’re less likely to flag a problem in a group meeting than they would in a private conversation. This means your sensing mechanisms have to be deliberately broader than they would be in a co-located environment.

A short, bi-weekly individual check-in — not a performance conversation, just a direct question like ‘What’s one thing that’s slowing you down right now that I might be able to help with?’ — surfaces issues that otherwise accumulate quietly until they become crises. The goal isn’t to micromanage. It’s to ensure the feedback loop is working.

If you’re a director reading this with a team of managers beneath you, the communication system above is only half the challenge. The other half is ensuring your managers are actually carrying the message forward — not just filtering it, or interpreting it into something subtly different at each level.

This is where emotional intelligence becomes a leadership selection and development question. Daniel Goleman’s framework identifies relationship management — the ability to inspire, influence, and develop others — as the domain that determines whether a leader can actually move a team through change or just communicate at them.

Managers with strong relationship management skills can translate strategic ambiguity into team-level clarity without spinning, minimizing, or catastrophizing. Managers who are managing their own anxiety about the change tend to transmit that anxiety downward, even when their words are technically reassuring. The emotional signal and the verbal signal are both real — and when they conflict, people believe the emotional one.

Building buy-in with your manager layer means doing three things explicitly: involving them in shaping the communication, not just receiving it; giving them language they can use with their own teams; and checking in on how they’re personally experiencing the change, not just how they’re executing the messaging. A manager who feels informed and supported is a communication multiplier. A manager who feels managed and excluded is a liability you may not discover until the damage is done.

The goal of all of this isn’t a team that doesn’t have questions or concerns. It’s a team that can act on what they know while holding the uncertainty that exists without letting it stop them.

In practice, confident execution during ambiguity looks like: individuals making the calls within their scope without waiting for permission they already have; managers flagging real blockers rather than everything that feels uncertain; and the team’s output quality holding steady even as the context around it shifts.

That’s not luck. That’s the result of a leader who built the communication system before the ambiguity arrived, who maintained the rhythm when it did, and who was honest — including about their own limitations — throughout.

The teams I’ve seen navigate change well are almost never the teams that had the most information. They’re the teams whose leaders showed up consistently, communicated honestly, and stayed emotionally present when the path wasn’t clear. That’s not a framework. That’s a posture. And it’s learnable.

The goal of all of this isn’t a team that doesn’t have questions or concerns. It’s a team that can act on what they know while holding the uncertainty that exists without letting it stop them.

In practice, confident execution during ambiguity looks like: individuals making the calls within their scope without waiting for permission they already have; managers flagging real blockers rather than everything that feels uncertain; and the team’s output quality holding steady even as the context around it shifts.

That’s not luck. That’s the result of a leader who built the communication system before the ambiguity arrived, who maintained the rhythm when it did, and who was honest — including about their own limitations — throughout.

The teams I’ve seen navigate change well are almost never the teams that had the most information. They’re the teams whose leaders showed up consistently, communicated honestly, and stayed emotionally present when the path wasn’t clear. That’s not a framework. That’s a posture. And it’s learnable.

References

1. Edmondson, Amy C., and Kathryn S. Roloff. “Leveraging Diversity Through Psychological Safety.” Rotman Magazine, Fall 2009, 47–51. Adapted from Team Effectiveness in Complex Organizations: Cross-disciplinary Perspectives and Approaches. New York: Routledge Academic, 2008.
2. Goleman, Daniel. Working with Emotional Intelligence. New York: Bantam Books, 1998. EQ framework adapted in Session 2: Emotional Intelligence, University of Tampa BUS 698 Leadership Development Program, Fall 2024.
3. Deloitte. Deloitte Global Millennial Survey 2020. Deloitte Development LLC, 2020. https://www2.deloitte.com/global/en/pages/about-deloitte/articles/millennialsurvey.html
4. Chrysalis Consulting. “Leadership, Not Likership.” Breakout Session, Fall 2024. Facilitated by Karen Kralios and Susan Vroman.
5. University of Tampa, TECO Energy Center for Leadership. BUS 698: Modern Advances in Leadership. Sykes College of Business, Fall 2024. https://www.ut.edu/academics/sykes-college-of-business/centers-and-institutes/teco-energy-center-for-leadership/leadership-development-programs
6. For additional reading on leading distributed teams through change, see: Kotter, John P. Leading Change. Boston: Harvard Business Review Press, 2012. https://hbr.org/books/kotter