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Leadership Communication Problems in Startups and What to Do About Them

David Sherry
8 min read
Leadership Communication Problems in Startups and What to Do About Them

One of the least talked about, but most prevalent problems within companies are communication and people issues.

Almost every founder I know has been through some type of communication issue with a co-founder or team member. These often lead to messy “breakups,” difficult and complex situations around equity or ownership, and periods within a company where communication issues cause a drag on productivity.

While we focus so much on tactics, the personal side of business can’t be avoided. When Co-founders disagree and start to lose trust in one another, how do you resolve conflict?

I’ve made my fair share of mistakes here. I’ve also had really amazing relationships with business partners where I felt supported and like I could be fully open with the other person without any fear.

I wanted to share how communication can break down at startups in leadership and what to do about it. Oftentimes, it's people problems that kill companies. Sure, product-market fit isn't reached or you run out of funding or you don't grow, but it's the people who are responsible for those things that we're assuming are fully aligned and working to their fullest abilities. This is often not true.

Dysfunction at the level of people will cause dysfunction at the level of product.

There are a whole host of ramifications of people's problems within the business.

Co-founders disagree, and the business suffers. Leadership lacks clarity, and the team is confused and frustrated about their lack of direction. Team members leave their roles because they start to doubt if they have a future there... etc.

The problems within leadership communication can start at any stage of the business:

  • People problems and miscommunications can happen because of growth. When companies grow quickly and roles need to re-arrange, it's no longer the same business.
  • Communication problems can also happen when there is a lack of growth. When the business gets tough, people get stressed, and so challenges can arise there too.

When problems between co-founders or leadership start to emerge, usually they have been brewing under the surface for a long time. They start to present signs that become increasingly obvious to the stakeholders.

Here are some symptoms that problems are occurring:

  • A member of leadership checks out: That co-founder who previously was involved in a multitude of projects starts to show up less, and “give up” on projects due to a sense of futility.
  • A member of leadership suddenly checks back in: A leader, previously giving space to team members to handle their work suddenly and frantically is getting hands-on in areas that they have been out of the loop, doing more harm than good.
  • Communication happens in silos: Discussions begin to happen about different members of the team without having them in the room. Leaders take and play sides, it becomes increasingly difficult to tease out what is truly going on.
  • Miscommunications stack up: Because of this siloed communication, miscommunications compound. This erodes trust and credibility, and decisions happen based on preconceptions and assumptions over facts and realities.

Returning to Alignment:

So, what can be done about challenges happening in leadership? And how can you begin to repair the relationships, and put the business back on a track of alignment?

People first, Responsibilities + Roles Second.

While it’s tempting to push through fixes and changes about roles, responsibilities, and projects (the work) we need to remember that the miscommunications and misalignments are people-first problems, not fixable by purely shifting into “fix it with process and workflows.”

This means that we need to build in time for there to be time for person-to-person discussions that are separate from decisions about role changes.

So, how do you being to do that?

Re-Open Channels for Honest Feedback.

Difficult conversations need to be had, and misunderstandings need to be addressed. Start by booking a time for a meeting with

You do a disservice to someone's personal growth when you avoid giving them feedback about how their actions lead to negative consequences within the organization.

If your team member has a true intent to create success aligned with the benefit of the business, then humility is needed to begin to help someone see how they might change their approach to create better results within the organization.

Host a meeting focused on clearing up personal conflict.

The purpose of this meeting is to bring into the light feelings which may have not been expressed about previous events. So, rather than having them stay bottled up, bring them to the surface so that you can get back to neutral.

Most times, conflict comes from misunderstanding. We are projecting how we imagine the other person feels, or what they think, rather than truly understanding it.

In this meeting, you can have each of the conflicting parties bring a few “moments” that they are struggling with, within the organization and within the team. Having specific moments to point to will help make points concrete.

Give each person time to go through and share moments or situations, and have them speak to what they felt were the consequences of that situation or moment. It’s the consequences that are the most revealing.

“When you did this… it made me feel like X”

“When this decision was made, I believe it lead to Y”

“When no action was taken here, it left me to do Z”

This is not about blaming one another, it’s about getting to the root of how specific actions or interactions are creating conflict.

When someone’s actions are leading to negative effects, these negative effects need to be put into the light to see more clearly. This conversation is not about personal attacks, it’s about clearing up areas where miscommunications and misperceptions have happened.

To set the stage for this conversation, I think having some ground rules can help:

  1. Start the meeting with something positive. Ask a question that prompts everyone to share. One example might be “What are you most excited about with the future of the business?”
  2. End the meeting with a handshake or hug it out: Have it be known ahead of time that this is the case. If virtual you can virtually high-five.
  3. Let people have their time + space, but not more. Time constrain people’s sharing to appropriately get what they need off their chest without overdoing it or moving into personal attacks. Keep on track.
  4. Leave the meeting with next steps. It’s likely that more than one discussion is needed to re-align. Leave the meeting with a clear next time to meet, which doesn’t have to be immediate. It’s ok to let dust settle a bit, so plan to speak again in the next week or two.

Host a meeting, focused on roles + responsibilities.

At the root of most team miscommunication is a misalignment of roles and responsibilities.

Maybe roles were not set ahead of time, and just assumed. Or maybe roles and responsibilities have change throughout the growth of the organization. Clarity about roles and responsibilities will help people stay out of conflict, if and only if…

  1. Roles are clear – People know what lane they are in.
  2. Responsibilities are clear – People confirm that they are taking responsibility.
  3. Accountability is expected – People are aware that they are accountable to the responsibilities that they have chosen to own, and know that roles may be re-assesed if performance isn’t meeting expectations.
  4. Trust is Given – People are given the adequate trust to perform their roles and responsibilities to the best of their abilities. This means not stepping into a role that is not your own and giving ample opportunity and space for team members to be successful.

At the end of the meeting, you will have wanted to define the current roles and responsibilities are for each person on the leadership team.

This includes; Who is responsible for what? How are decisions made? Who is in which role? And how will communication happen in the future if expectations are not being met?

Focus on strengths + weaknesses

When a person is in a role that suits their strengths, they are more likely to be successful. Part of the discussion around roles and responsibilities is to ensure that team members are in roles that they can be successful in.

By positioning the discussion around strengths and weaknesses, team members can have an open discussion about roles + responsibilities that align with their abilities.

Neutral, third parties can help

Ideally, there is a third co-founder, board member, or leader who is in a more neutral position with any conflict between 2 other team members.

The role of this person is to help with re-alignment by being honest about what they see. The neutrality of this team member is the key. Because two parties who may be in conflict will have trouble seeing eye to eye, the neutral third party can help provide a perspective that removes some of that bias, and is more likely to be heard. It’s difficult to have two people immediately change how they feel or what they have previously concluded about the other person.

If you don’t have a neutral third party to help with these discussions, you can always look to bring one in via a coach, mentor or advisor. Have them get in touch with everyone separately before the meetings to get context, before jumping into the meetings.

Alignment conversations are difficult, but things can get better.

It’s normal for this to be difficult, and that’s OK. It’s also normal for this type of problem to be tiring and draining. You want to focus on the work and build a great company, not get bogged down in people issues… however, the reality is that people problems are a part of doing business and building successful teams and therefore successful businesses.

It’s 100% possible that you can resolve and improve communication issues. The king thing to know, however, is that this is a process that takes time. Sometimes you have a conversation that feels like it goes NOWHERE but then a month or two later you realize that things actually started to shift as a result of it.

Ultimately humility, and truly hearing feedback from others, is what leads to growth.

You don’t want to admit it, but there is likely a part of any situation in which you have contributed to any misunderstanding. When conflict happens, we tend to shut down, feel sensitive, be less honest than we should to avoid hard conversations… the list goes on. Humility is having the ability to ask “where can I grow in this situation?” as well as being open enough to truly listen to your team members or co-founders.

When you truly listen in these conversations, you get a better sense of where other people are struggling. Not only that, but if you truly listen, you’ll hear aspects of your own communication or responsibilities that could improve.

Teams that continue to struggle will spiral on these issues because people don’t accept the personal responsibility necessary to grow. Those teams that see every conversation as a way to make things better, make relationships stronger, realize personal flaws that they can improve upon, will keep seeing trust and communication lines improve.

What hard conversations are you willing to have?

Those difficult conversations, the ones you want to avoid, are probably the very thing that will create the most progress in your relationships. The more we cover up, the deeper and more tangled problems at the surface become.

Being open and staying open while listening as you bring issues to the surface is a practice that we can continue to cultivate. If you’re in a state of conflict today, see where you can bring diffiuclt topics into the light. And, as you re-open channels of communication with honesty, reflect on where you can grow through the discussions.

Last, if you’re in the midst of difficult communication issues at work, feel free to hit reply. I’m curious how you’re feeling, what you’ve found works, or where you get stuck,

As always, let me know if I can help,

Xx David

BusinessInterpersonal Communication