RelationshipOps of the Week #26.
Design System Agency
|
Apr 17, 2026
“Most of our best opportunities don’t start with a pitch… they start with a conversation that already has momentum.”
“Most of our best opportunities don’t start with a pitch… they start with a conversation that already has momentum.”
Symon Oliver.
This week, we’re featuring Symon Oliver, Founder & Design Director of Tennis Digital… a B2B web and product design agency known for its clarity-first approach to complex digital problems.
Symon focuses on developing strategies for technical, strategic, and design implementation that meets their clients’ immediate and long-term needs and are later translated into actionable and measurable objectives. At the agency level, he empowers the team to make confident decisions that steer positive project outcomes.
What makes him especially relevant to this series is how he thinks about relationship-building… not as a supplement, but as the work itself.
For Symon, staying visible and being decent has opened doors with past collaborators, new decision-makers, and teams who already trust the way he thinks. And Tennis has stayed lean and focused because of that mindset… converting conversations into contracts without relying on funnels, fancy pitches, or scraping cold leads.
Let’s dive into how he stays connected with contacts that matter.
Staying Visible, Being Decent.
Leonard Chin: What’s an instance when a relationship led to a big win or a really great opportunity for your business?
Symon Oliver:
“Running an agency like Tennis has taught me one thing faster than any business book ever could: relationships aren’t a nice-to-have. They’re the work.
We’re a B2B web and product design agency. We sell thinking, judgment, and follow-through. None of that travels well through cold outreach. It travels through people who already know how you work, or at least know someone who does. That’s why most of our best opportunities don’t start with a pitch. They start with a conversation that already has momentum.
A recent example sticks with me because it was almost boring in how simple it was.
Someone I’d worked with before switched roles. I sent a congrats, we reconnected, and the next day they asked for a one-pager. A month later, we were working together again.
That’s it. No master plan, no funnel, just staying visible and being decent.
That story isn’t special because it’s rare. It’s special because it keeps happening. Old contacts resurface, a comment on LinkedIn turns into a DM, which turns into a call, which turns into work. Not every time, but often enough that the pattern is evident.”
Small and Survivable.
Leonard Chin: What's your daily/weekly routine for maintaining relationships that help your business?
Symon Oliver:
“The funny part is that I’m not naturally great at maintaining relationships.
My role at Tennis pulls me deep into operations, systems, delivery, and client work. Days fill up fast. Keeping up with people can feel like a background task that never quite reaches the top of the list. I’m lucky to have a business partner, which means we can tag-team relationship energy when one of us is underwater. Even then, it’s a stretch.
So I stopped pretending I’d magically become someone who “just keeps up with everyone.”
Instead, I built something small and survivable.
Most of my business relationships live on LinkedIn, whether I like it or not. So that’s where I focus my attention. My routine is simple. I check messages. I respond properly, not with drive-by replies. I make a few new connections if there’s a real reason. Then I scan the Network tab and look for signals. Job changes. Work anniversaries. People resurfacing in new contexts.
Those moments are opportunities—not sales opportunities, but human ones. “Hey, saw you moved roles—how’s it going?” is enough. If nothing comes of it, that’s fine. If something does, great. Either way, the connection stays warm.
Is it perfect? Not even close. Some weeks, I miss it entirely. Some weeks, I do the bare minimum. But it’s better than relying on guilt and good intentions, which don’t scale at all.”
Habits Need Runway.
Leonard Chin: What tips would you give to your younger self around relationships and how they impact business?
Symon Oliver:
“If I could give my younger self advice on this, it wouldn’t be about networking harder. It would be about habits and patience.
I used to think you could spin up a habit at full speed. Decide you’re “good at relationships now” and act accordingly. That never worked. Starting good habits is harder than breaking bad ones, and pretending otherwise just leads to burnout.
Habits need runway.
The shift for me was thinking in increments. One old contact a week. Do that for three months to get into the rhythm. Add it to your calendar so you don’t have to negotiate with yourself every time. Once that feels normal, increase to twice a week. Slowly build toward a pace you can actually sustain while running a business and staying sane.
Your calendar is an underrated tool. It’s not just for meetings, it’s for protecting patterns you care about, and shaping new habits. Reminders beat motivation every time.
But tools aren’t the point. Consistency is. Especially on days when you don’t feel like it, or when the payoff feels abstract. You don’t see the return right away, but relationships compound over time. Then one day, someone you congratulated months ago sends a note that turns into real work.
That’s when it clicks.
This stuff isn’t flashy. It won’t show up neatly in your metrics dashboard. But if you run a services business and you’re ignoring relationships, you’re making things harder than they need to be.
Sometimes the biggest wins start with saying “hey, it’s been a minute, how are things?” and actually meaning it.
Key Takeaways.
We’re glad to have Symon Oliver with us on this week’s series, but if anything, here are the few key takeaways:
Relationships are the work. Symon’s biggest opportunities start not with pitches, but with warm re-connections that lead to real conversations.
LinkedIn is the daily beat. Instead of chasing perfection, he uses light, repeatable LinkedIn rhythms to keep connections alive without burning out.
Scale through habit, not hype. One warm contact a week beats over-engineered systems. Small efforts add up, and over time, they compound into real work.
That’s all for this week.
If you're open to sharing your experiences in one of our future articles… or know of someone who is, feel free to drop me an email here.
Author.
Leonard Chin
Follow me on LinkedIn.
Symon Oliver.
This week, we’re featuring Symon Oliver, Founder & Design Director of Tennis Digital… a B2B web and product design agency known for its clarity-first approach to complex digital problems.
Symon focuses on developing strategies for technical, strategic, and design implementation that meets their clients’ immediate and long-term needs and are later translated into actionable and measurable objectives. At the agency level, he empowers the team to make confident decisions that steer positive project outcomes.
What makes him especially relevant to this series is how he thinks about relationship-building… not as a supplement, but as the work itself.
For Symon, staying visible and being decent has opened doors with past collaborators, new decision-makers, and teams who already trust the way he thinks. And Tennis has stayed lean and focused because of that mindset… converting conversations into contracts without relying on funnels, fancy pitches, or scraping cold leads.
Let’s dive into how he stays connected with contacts that matter.
Staying Visible, Being Decent.
Leonard Chin: What’s an instance when a relationship led to a big win or a really great opportunity for your business?
Symon Oliver:
“Running an agency like Tennis has taught me one thing faster than any business book ever could: relationships aren’t a nice-to-have. They’re the work.
We’re a B2B web and product design agency. We sell thinking, judgment, and follow-through. None of that travels well through cold outreach. It travels through people who already know how you work, or at least know someone who does. That’s why most of our best opportunities don’t start with a pitch. They start with a conversation that already has momentum.
A recent example sticks with me because it was almost boring in how simple it was.
Someone I’d worked with before switched roles. I sent a congrats, we reconnected, and the next day they asked for a one-pager. A month later, we were working together again.
That’s it. No master plan, no funnel, just staying visible and being decent.
That story isn’t special because it’s rare. It’s special because it keeps happening. Old contacts resurface, a comment on LinkedIn turns into a DM, which turns into a call, which turns into work. Not every time, but often enough that the pattern is evident.”
Small and Survivable.
Leonard Chin: What's your daily/weekly routine for maintaining relationships that help your business?
Symon Oliver:
“The funny part is that I’m not naturally great at maintaining relationships.
My role at Tennis pulls me deep into operations, systems, delivery, and client work. Days fill up fast. Keeping up with people can feel like a background task that never quite reaches the top of the list. I’m lucky to have a business partner, which means we can tag-team relationship energy when one of us is underwater. Even then, it’s a stretch.
So I stopped pretending I’d magically become someone who “just keeps up with everyone.”
Instead, I built something small and survivable.
Most of my business relationships live on LinkedIn, whether I like it or not. So that’s where I focus my attention. My routine is simple. I check messages. I respond properly, not with drive-by replies. I make a few new connections if there’s a real reason. Then I scan the Network tab and look for signals. Job changes. Work anniversaries. People resurfacing in new contexts.
Those moments are opportunities—not sales opportunities, but human ones. “Hey, saw you moved roles—how’s it going?” is enough. If nothing comes of it, that’s fine. If something does, great. Either way, the connection stays warm.
Is it perfect? Not even close. Some weeks, I miss it entirely. Some weeks, I do the bare minimum. But it’s better than relying on guilt and good intentions, which don’t scale at all.”
Habits Need Runway.
Leonard Chin: What tips would you give to your younger self around relationships and how they impact business?
Symon Oliver:
“If I could give my younger self advice on this, it wouldn’t be about networking harder. It would be about habits and patience.
I used to think you could spin up a habit at full speed. Decide you’re “good at relationships now” and act accordingly. That never worked. Starting good habits is harder than breaking bad ones, and pretending otherwise just leads to burnout.
Habits need runway.
The shift for me was thinking in increments. One old contact a week. Do that for three months to get into the rhythm. Add it to your calendar so you don’t have to negotiate with yourself every time. Once that feels normal, increase to twice a week. Slowly build toward a pace you can actually sustain while running a business and staying sane.
Your calendar is an underrated tool. It’s not just for meetings, it’s for protecting patterns you care about, and shaping new habits. Reminders beat motivation every time.
But tools aren’t the point. Consistency is. Especially on days when you don’t feel like it, or when the payoff feels abstract. You don’t see the return right away, but relationships compound over time. Then one day, someone you congratulated months ago sends a note that turns into real work.
That’s when it clicks.
This stuff isn’t flashy. It won’t show up neatly in your metrics dashboard. But if you run a services business and you’re ignoring relationships, you’re making things harder than they need to be.
Sometimes the biggest wins start with saying “hey, it’s been a minute, how are things?” and actually meaning it.
Key Takeaways.
We’re glad to have Symon Oliver with us on this week’s series, but if anything, here are the few key takeaways:
Relationships are the work. Symon’s biggest opportunities start not with pitches, but with warm re-connections that lead to real conversations.
LinkedIn is the daily beat. Instead of chasing perfection, he uses light, repeatable LinkedIn rhythms to keep connections alive without burning out.
Scale through habit, not hype. One warm contact a week beats over-engineered systems. Small efforts add up, and over time, they compound into real work.
That’s all for this week.
If you're open to sharing your experiences in one of our future articles… or know of someone who is, feel free to drop me an email here.
Author.
Leonard Chin
Follow me on LinkedIn.