Hey there. Happy Saturday! Today, I want to share some thoughts on building trust as a service business.

Most advice about building trust sounds the same: be consistent, give value, show up regularly, be authentic. Build relationships slowly over time.

I spent years following this advice. And you know what? It is only part of the picture.

Then I started noticing something strange in my own experience. Some professional relationships took years to develop. Others happened in weeks. A few locked in after a single conversation.

The difference wasn't how much value I provided or how consistent I was. It was about timing - and recognizing that trust operates in three completely different modes depending on someone's emotional and mental state.

Here's what I discovered.

The problem with "building" trust

The word "building" suggests a linear process. Do A, then B, then C, and trust gradually forms. Stay visible. Give consistently. Be patient.

But that's not exactly how it actually works.

When I just started my design career, I once spent months trying to connect with a founder at a design studio. We had coffee and I had an idea of joining his company just for a summer. I know it’s not wise to continue to ask for more after our first meeting, so I waited. 

Then I get to connected with a mutual connection who knew the previous founder well. I asked for an introduction/recommendation 2nd time - even though I'd already met the previous founder once. This time, with borrowed credibility, we connected again. I didn't pitch anything. I asked if this founder can speak to my students and share his firm’s work.

He said yes. That led to another conversation. Then it became a fellowship to spend a summer working with their team. Eventually, this founder became a mentor who I still talk to years later.

I didn't "build" that trust through consistency. Instead, tested for it, then borrowed it, then amplified it at specific moments. So here’s what I call my exact “trust building” formula. 

Phase 1: Test at their high points

The biggest breakthrough came when I realized: people are most receptive to new connections during inflection points.

Promotions. Funding announcements. Speaking engagements. Product launches. These are moments when someone is in a heightened emotional state - energized, open, proud. Their guard is down, and they expect people reach out to them.

A founder I wanted to work with announced their Series B funding. Instead of just congratulating them (which 50 other people probably did), I reached out with a question: "I'm curious how you're thinking about team structure now that you're scaling. I'm researching how AI-era startups approach design resources differently."

Not a pitch. A question that lets them be the expert.

We talked for 30 minutes. Turns out we knew tons of people in common, we even grew up in the same city. We both had similar views on how early-stage companies should operate.

I didn't sell anything. Even after the call, I just shared some research I'd done and writing about design leadership and thoughts I have about design problems at startups. Basically said: if you ever want feedback on your product or need someone to think through design challenges, I'm here.

A few weeks later, the founder reached out. They needed urgent design help and didn't have an in-house team. That’s the result I wanted, but we didn’t get there right away.

I didn't approach them at a random time. I showed up at an inflection point with something specific (not just "let's connect"), then tested for receptivity.

The 3 entry strategies to build initial trust

Once you've identified an inflection point, you have three moves:

1. The direct shot

Use this when it's your only chance - conferences, one-time meetings, someone traveling through town.

I once attended a conference where a female leader I admired gave a talk. After she finished, I walked straight up: "I teach in the design field and have three months every summer. I'd love to contribute to your organization with my design skills in any capacity that's helpful."

She handed me her business card. Told me to reach out through email. We emailed back and forth. I did a summer fellowship with her team.

Direct worked because: (1) it was surprising - nobody else was making an ask like that, and (2) there was no next time. She was traveling through. It was now or never.

2. The strategic question

Use this when you need something but can't ask directly yet. You position yourself through curiosity that lets them shine.

The Series B founder question about team structure wasn't really about research. It was designed to: (1) let him talk about his expertise, and (2) reveal mine without pitching.

People want to feel valuable. Sometimes asking them to give (insights, advice, their story) builds more trust than offering your services.

3. Borrowed trust

Yes, it’s like a warm intro. Use this when a direct approach won't work. Engineer an introduction through someone who already has their trust. Even if you have connected with the person, and you need a reason to re-connect again.

This is what I did with the mentor. I waited until a mutual connection mentioned his name, then asked for a second introduction. I was essentially arbitraging trust - borrowing credibility from an existing relationship.

Reading the signals (and knowing when to walk away)

Here's what most networking advice gets wrong: it assumes every connection is worth pursuing if you're just consistent enough.

That's not true.

After you make your move - whether it's a direct ask, a strategic question, or a borrowed intro - you need to read mid-conversation signals to decide if this is worth investing in.

Green signals mean keep going:

• They ask follow-up questions

• They share more than necessary

• They extend the conversation naturally

• They offer things unprompted

• Their energy shows up

Red signals mean walk away completely:

• Short, closed answers

• No emotional response

• Checking the time, trying to escape

• Not engaging with your questions

• The whole thing feels forced

I once scheduled a call with someone after weeks of trying to coordinate. I was excited - we had mutual connections, and seemed aligned on paper.

Fifteen minutes in, I realized: this wasn't going anywhere. No matter what I asked, she sat there with minimal response. No energy. She kept glancing away. In exactly 13 minutes, she said she had another meeting.

We're in the same community. Lots of mutual connections. I never approached her again. The rule: Test once. Read the signals. If it's red, let it die - even if you're in the same circles.

Not everyone is your person. And that's okay.

The initial stage to start that trust building process is the hardest, and it’s also why most people fail to connect. Once passing that stage, it’s important to realize that deepening trust through every small interation.

Phase 2: Deepen at their normal moments

Once we passes the signal trust test, you don't stay in touch through "regular check-ins" or "just touching base."

You deepen trust by over-delivering on every single small ask.

An engineer leader I worked with briefly started his own company recently. Initially bootstrapped, no funding. Every few weeks, he'd ask something very small:

"Hey Li, can you look at my logo concept with GPT?"

I didn't just say "looks good/bad." I told him what could be better and offered to create him 3 new logos. For free.

"Just launched the product. Can you give feedback?"

I didn't just click around and say nice things. I recorded a full video walkthrough - went through every screen, explained my thinking, suggested improvements.

"Posted this on social media. Mind sharing it?"

I shared it immediately with thoughtful quotes.

None of these were big asks. But each one was a trust test. Will you respond fast? Will you do the minimum or go further? Will you act like this matters even when there's no money involved?

I've worked with many contractors and vendors where I have to chase them for responses. Wait days for simple answers. Constantly manage them even on small things. That kills trust.

The opposite - responding timely, going 10x further than requested - compounds trust faster than any amount of "consistent networking."

Small asks are trust tests in disguise. Treat them like they're the most important request of the day.

Phase 3: Lock in at their low points

Here's the most counterintuitive part: Real trust isn't built when everything is smooth. It's forged during a crisis.

I had a client with a regular stream of projects. Professional relationship, good communication, solid trust. Then one week: "We have a conference in three days. We need materials designed in the next 48 hours. Can you make it happen?"

We made it happen. Stayed up late. Delivered on time. They looked amazing in front of their team and leadership.

That's when the relationship changed. I wasn't just a good vendor anymore. We were the team they could count on when things got chaotic.

Another time, there was a miscommunication. A client thought we were delivering both design and development, but I thought we are only delivering designs. We only had design capacity at that time, and the deadline was in two days.

He panicked. Scrambled to find a developer. I'd already finished my part - technically, I was done.

But I didn't disappear. I stayed available the entire time. Answered questions immediately. Offered to adjust designs and also help him look for a developer. Basically said: I'm always here until everything is resolved, even though my piece is done.

When it was over, he told me that my availability meant more than the design work.

The crisis playbook

When things go wrong - deadlines compress, mistakes happen, priorities shift wildly - most vendors protect their boundaries: "I need more time." "This wasn't in the original scope." "Let me check my calendar."

All reasonable responses. All trust killers in a crisis.

During a crisis, normal rules don't apply.

When someone is drowning, they don't need you to explain why something isn't your fault or set appropriate boundaries. They need you to not become another problem.

Your job in a crisis:

• Be constantly available (even if it means staying up late)

• Over-communicate (so they don't have to chase you)

• Absorb their stress without breaking (even if they're short or rude)

• Remove yourself from their list of problems

Here's the hard truth: when founders or leaders are in fire mode, they get sharp. They say things that don't sound nice. They're not thinking about your feelings - they're trying to survive the deadline, save the launch, fix the disaster.

If you take it personally, push back, or require emotional management during chaos, trust breaks. If you stay calm, keep delivering, and don't add drama to their crisis, you earn lifetime trust.You build the most trust when they're at their worst.

The three-state system

Here's what nobody tells you about trust: most people try to build trust the same way regardless of context. They're consistently authentic, they network regularly, they give value steadily.

But I've learned that trust works differently when you meet the other side at a different state:

At high points, people want to be approached (but strategically, with something specific).

At normal points, people want you to exceed expectations (quietly, consistently, without needing management).

At low points, people want you to be unbreakable (absorbing chaos without adding more).

The 4 trust principles I live by

The asking: Sometimes asking them to give (insights, advice, expertise) can build trust more than you think - especially when you don’t have much to offer.

The speed: Trust can happen in a month or take years. It's not about how long you invest - it's about catching the right moment with the right move.

The crisis: You earn the most trust when they're at their worst. Everyone thinks trust is built during good times. It's actually locked in during bad times.

The walking away: Building trust means knowing when NOT to build trust. Test once, read signals, walk away if it's red. You're not trying to build trust with everyone.

The real formula

Trust isn't built. It's tested, then borrowed or amplified at inflection points.

You're not creating trust through force of will or consistency. You're finding the moments where trust can form naturally (inflection points), widening those openings through extreme responsiveness (over-delivery), then cementing them permanently when pressure hits (crisis).

Thinking about this framework has transformed how I approach relationships in service businesses—where trust isn't just nice to have, it's the currency that closes deals.

I'm curious: Which of these three phases resonates most with your experience? Have you noticed trust locking in during a crisis you handled well?

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