How To Communicate And Connect With Others As A Founder (Leader)

Here is a list of ideas and tips on how to connect better with others through communication.

As a founder (and a leader), you will be communicating every single day. Whether it’d be your team, your customers, your investors, your partners, your significant other and even to yourself (this is important!), the cycle is non-stop. It is your responsibility as a Founder to share your vision day in and day out and the better your stakeholders understand you, the more effective you will be.

With time being one of the most important assets that you will ever have, it is crucial to continue to develop your communication skills so that everyone else will be able to understand you and therefore support your needs in a more productive way (equally important to support theirs too, don’t forget - their time is just as important as yours). When time is such a precious commodity, being able to succinctly express yourself is a real skill. Here are some tactics and tools that I’ve found helpful in my past experience and am still learning to do better. 

If you have any ideas, feel free to share with me or @wincewong and I’ll add to this post.

Everyone is different

One of the first things to keep in mind at all times is everyone has a different experience to you. They grew up in different cultures, they studied different subjects, they worked at different companies and even have different music taste than you. As humans, we like to generalize and put people into buckets (Engineer, Designers, MBAs, VCs, Corporates etc etc), because it makes our lives easier. Our brain can only process a limited amount of information at a time and we’re always looking for shortcuts to make things more efficient. By generalizing, our brain is telling us to communicate a certain way. If we keep this in mind at all times, we will seek to understand rather than seek to tell.

Be Interested

We need to spend time understanding our audience, their context, their motivation and more importantly who they are as a person. If you haven’t met or worked with this person previously, it’s even more important to spend a little bit of time researching their backgrounds and asking questions (setting right expectations) for the context of the conversation. This should happen prior to the meeting over email at a high level and then at the start of the call, video conference or in person meeting. Make sure you spend some time getting to know the person - be actually interested in them - where they’re from, their interests, their goals, potential outcomes of the chat and react appropriately. It’s pretty clear when small talk is disingenuous so make sure you can also share more about yourself as part of your conversation is a key way to connect.

Know Yourself

There are a lot of big personalities in the business world (Steve Jobs, Elon Musk, Mark Zuckerberg etc) and many times through school, through media, through work - we’re naturally trained to emulate (or even worship them). This is because that’s what success is portrayed to be like (a perfect example here is Elizabeth Holmes of Theranos). It’s important to remember that you’re not seeing the full self of the person you read in the newspaper or watch on stage. Knowing who you are deep inside, your core, your values and your strengths will give you the confidence to connect and communicate the way that feels most natural to you - this will be reflected in your communication style and will naturally draw people to you.

Watch out for cues

Body language is obviously a crucial form of communication. It’s also a form of communication that requires you to be mindful of since your muscle memory and brain may not be in sync all the time. If you’re annoyed during a meeting, it can show up in your face, in the way you sit and even move your hands. Whilst it’s important to be animated at times to show energy, you also don’t want to give a perception of anger or disapproval when you’re trying to build trust and empower your team. One way to manage this to create an action that changes how your body reacts. For example, if you know that when you’re angry, you tense up, try stretching or moving your fingers - it’ll help change the mood.

Follow Up

One of the most underrated skills for anyone when communicating and connecting with others is the ability to follow up on a regular basis. If there was a next step or action item from your conversation - follow up! Trust me - the other person will appreciate it and you’ve already established a positive impression on them. A tip on how to do this is to create your own CRM spreadsheet. It doesn’t have to be as scary or as formal as creating a salesforce instance. You also don’t want to make it like a job or so transactional that it feels forced (the other person will sense this!). In general, have a high level understanding on what the person is interested in, where they’re from.

Over Communicate 

It can get frustrating at times to have to explain yourself multiple times a day - maybe even in the same conversation especially if you have other priorities to get to. You might be wondering - “Why don’t they understand my vision!” or “This is a simple concept - why do I have to explain myself again.” You are living your company on a daily basis and it is what matters to you dearly but other folks also have their own priorities in life. There are two ways to solve this.

  • Get them to understand your vision and care more about your purpose - naturally when people care more and can see how it relates to them - they will figure it out themselves
  • Help them understand, share with them articles that explain the concepts differently. Write down your thoughts and share that. People have different approaches to learning so being able to identify how it resonates is crucial. 
  • Don’t ever get frustrated or angry, it’ll only make the situation worse in the future. 

Keep it regular

It’s important to ensure who you’re working with have a sense of rhythm and structure. Try not to have a ton of ad-hoc conversations / meetings can overwhelm your team especially without the right context. They may not understand why it’s required and it interrupts their workflow especially if you need them to change priorities (or worse, they don’t know how to prioritize). This causes confusion, the team feeling overwhelmed and lower productivity. Ad-hoc meetings can be leveraged for anything really urgent but make sure you set the right context and expectations.

Better to be honest

It’s better to be honest when having conversations with your team, with investors or customers. Set the right context, be willing to listen but also provide your thoughts and feelings. Note that being honest doesn't mean being an asshole though - no personal attacks, no raising the voice , no using vulgar or inappropriate language. In the long term, it will help build trust with people you deal with and they would open up and reciprocate the same for you - making your relationship even stronger.

Be vulnerable

There is a need for founders to always feel like they are the rock of the organization and therefore have the pressure to feel like they need to make the right decisions or know the answers. This is practically impossible since no human can know everything. The willingness to say - ‘I don’t know the answer - what do you think?’ Or ‘let’s figure it out together’ or ‘Today has been stressful for these reasons’ is really helpful for your team to know that you’re also human, re-adjust expectations and roles that everyone plays in the team - which is to be supportive of each other.

Give Permission

Give you team time and permission to ask questions, lots of questions especially in the limited time that they have with you. If you assume they understand what you’re saying the first time, you probably will have to revisit the same topic again later on. 

You don’t have to run or take over every single meeting. If you’re in the meeting, people expect you to voice your opinion. If you don’t need to voice your opinion or don’t have an opinion then you probably don’t need to be in the meeting or you’re better off getting the information during your 1:1s or reading through any documentation at your own time. Don’t ever cancel your 1:1s, it illustrates the importance of spending time with your team which is a way of communication by itself.

By not reacting you are reacting

One of the biggest tips that I’ve been taught in the first few years of my professional life (and still incredibly difficult to do) is to not react during conversations. This could be during 1:1s or in team meetings. As a founder, the team generally defaults to you for decision making and providing your perspective. This is not scalable as your company grows. Providing the right context and vision is important but making decisions for your team is not. By not reacting and staying silent during meetings, you’re forcing your team (and giving them permission) to speak up, discuss and make decisions. Having others facilitate the meetings will give them the permission to run with it and establish trust with your team. Rotate facilitation on a regular basis so people will feel ownership for communication across the team. 

Be Kind to Yourself

Even the most charming person in the world is never going to please everyone and be able to connect with everyone. The reality is also you don’t need to. This is difficult for both extroverts and introverts. Extroverts may feel like they’re not the center of attention anymore and introverts may feel like they’re not trying hard enough to form connections. Either way, give yourself some slack because you’ve tried and you’re still a good person at heart.

Will share more on tools and other tips around communication (verbal, presentation, design and others) in upcoming posts. If you’re interested in learning more - feel free to subscribe to the blog! As always email me at if you want to discuss anything!