Working with Jon

Lead with the answer. If I ask you a question, start with the answer and then explain. Don't wind up to it. I don't need the backstory first — I need to know where we are, and then I'll ask follow-up questions if I want the context.

Email and Slack are my preferred channels. Both are great. Phone calls are good too, especially for anything nuanced or if we're working through something together. Text is fine for quick personal stuff, but don't use it as a work channel unless it's truly urgent.

Do not drop a meeting on my calendar the day of. This is a real one for me. Same-day meeting invites mess up my day. I plan my time, and a surprise meeting throws off whatever I had prioritized. If something is genuinely on fire, call me. Otherwise, give me notice.

Keep me updated as things happen. I want to hear from you daily, sometimes more often. Don't save things up for our next check-in if it's relevant now. A quick Slack message or email is perfect — it doesn't need to be a formal update.

Short meetings are usually fine. I'm in the details, so I usually don't need a long meeting to get caught up. The exception is when we're working through something new — a new concept, a strategic question, a discovery. Then let's take the time. But for status and alignment? Keep it tight.

Have an agenda. If you're scheduling time with me, know what you want to cover. I don't need a formal document, but I need to know what we're solving for before we start talking.

I decide fast. Sometimes too fast. I know this about myself. If you think I'm moving too quickly on something, say so — I won't be offended. But know that my bias is toward action over motion. I'd rather make a call, learn from it, and adjust than sit in analysis mode.

Easily reversible? Just do it. If a decision is easy to undo, make the call and let's align afterward. Don't wait for my permission on two-way doors.

Bring me your recommendation. Don't just bring me a problem. And don't just bring me a menu of options without a point of view. Tell me what you think we should do and why. I'll ask questions if your reasoning isn't obvious to me. If the options genuinely aren't obvious, then yes — spell them out. But lead with what you'd do.

One thing at a time. I say this a lot. We plan, we align, and then we execute step by step. Don't get anxious about step four when we're on step one. We'll get there. Have confidence that we can figure it out, but stay focused on what's in front of us right now.

Know what altitude you're at. This one is borrowed from Dalio, and I come back to it constantly. If we're having a 30,000-foot conversation, stay at 30,000 feet. If we're in the weeds at one inch, stay at one inch. People who jump between altitudes without signaling it — that tells me they're disorganized. If you need to shift levels, flag it. "Hey, zooming out for a second..." goes a long way.

It's me and you vs. the problem. That's always the frame. When I give you feedback, I'm focused on the behavior and the outcome we want — not judging you as a person. I expect the same from you. We need to create space between our work and who we are. A critique of the work is not a critique of you.

Be direct but compassionate. I don't want you to sugarcoat things, and I won't sugarcoat things for you. But there's a difference between being honest and being cruel. We can be straight with each other while still being decent about it.

Don't be afraid to tell me I'm missing context. If I'm reacting to something and you think I don't have the full picture — say so. Seriously. I want to hear it. But if I'm not missing context and I still see it differently, I need you to try and see it from my point of view. That's a two-way street.

New people sometimes misread my intensity. I'm aware of this. I come in focused, I ask direct questions, and I push hard on the work. People who are new to working with me can feel like they're being criticized personally. They're not. If you're feeling that, tell me and I'll recalibrate. But also know that my intensity is how I show up when I care — not when I'm upset.

You'll probably see it. My face and my tone tend to show when I'm stressed or frustrated. I'm not great at hiding it.

Don't take it personally. It's almost certainly not about you. Sometimes I need to drop everything and focus on the most important thing, and that thing might not be your thing. That's not a judgment on your work — it's just triage.

If you notice it, you can ask. "Is now a bad time?" is a perfectly fine question. Sometimes the answer will be yes, and we'll reconnect later. Sometimes the answer will be "No, let's push through this." Don't assume — just ask.

Do what you say you're going to do. This is number one. Full stop. If you commit to something, follow through. If something changes and you can't deliver, tell me before the deadline — not after.

Stay organized. Take notes. Track your own action items. Know what's on your plate and when it's due. If I have to chase you for things, trust erodes fast.

Ask questions in the moment. If something is unclear, ask now. Don't wait until tomorrow. Don't burn hours going down the wrong path because you didn't want to bother me. That's not initiative — that's wasted time.

Make assumptions and move forward. This sounds like it contradicts the last one, but it doesn't. If you truly can't get an answer right now, make a reasonable assumption, document it, and keep going. Don't let a missing detail stall the whole thing. Just flag what you assumed so we can correct if needed.

Flag things even when I'm copied. I get copied on a lot of email. I scan and read pretty much everything, but I don't always jump in or catch what matters most. If you see something in a thread that's off — a risk, a missed detail, a misalignment — don't assume I noticed it. Bump it up. Send me a separate note. "Hey, did you see this part?" goes a long way. Having someone on the team who knows when something is wrong and surfaces it proactively — that builds enormous trust with me.

Keep your monkey. If you've read Oncken's "Who's Got the Monkey?" — that's the framework. Bring me your recommendation, not your problem. Show initiative by identifying the issue, thinking through options, and proposing a path forward. That's what great looks like.

If you're someone I report to, here's what I need from you:

Paint the north star. Your job is to set the direction clearly enough that I can run with it. I don't need you in the details — I need to know where we're going and why.

Clear the way. If there are blockers outside my view — political, organizational, resource-related — help me see them or remove them. That's the highest-value thing you can do.

Make sure your part is ready. If I'm dependent on something from you, I need it on time. I move fast and I plan around commitments. If something shifts, tell me early.

Communicate as relevant things happen. If something changes in the landscape that affects my work — even if it's not fully formed yet — loop me in. I'd rather have early signal than a late surprise.

I respond quickly. And I expect the same energy, proportional to urgency. I'm not going to let things sit, and I appreciate people who match that pace.

I protect my early mornings. That's my peak energy time. I think best, plan best, and do my most important work early. Respect that block.

I believe in protected focus time for ICs. If you're doing individual contributor work, you should have uninterrupted blocks to do it. I'll advocate for that, and I expect you to protect it for yourself and your team.

I borrow from frameworks — a lot. Dalio's levels of altitude. Bezos's one-way/two-way door decisions. Oncken's Monkey Management. Jobs to Be Done. If I reference one of these and you're not familiar, ask me — I'm happy to share. These aren't buzzwords to me. They're how I think.

I'm an operator. I've built software, run production, managed P&Ls, written RFPs, designed brands, and set up LLCs. I'm not just a strategy person. I like being in the work. If something needs to get done and nobody's doing it, I'll do it myself — but I'd rather build a system where that's not necessary.

I'm not a natural networker. I care about relationships and I invest in the people around me. But I'm not going to work a room or play the schmooze game. I build trust through the work and through being real.