tend the orchard
coaching retainer
Steward what you've grown with someone who can keep up with the complexity.
For for founders and leaders who have created something substantial, but are carrying the vision alone.
You're good at this. So why does it feel like the business is running you?
You started it because you have real, valuable skills that you’re proud of. Then suddenly you had to learn to be the accountant, the HR manager, and the person who fixes the website when it breaks. You’ve figured most of it out because that’s what you do, but you feel pulled in so many directions at once that it’s hard to know what changes will actually make a difference. You're the end of the line. There's no one else to take responsibility, and no one to confide in who doesn’t work for you. You can't keep being the human firewall forever. Carrying everything alone isn't leadership, it's a slow-motion collapse.
You need to zoom out, and you need a fresh pair of eyes.
Tend the orchard is where we use systems thinking to solve problems at a business-wide level. I know how to hold complexity without getting lost in it, spot the patterns that the people inside the room can't see, and find the thread that connects everything back to what actually matters. The reason you got into this in the first place.
This retainer package is a genuine thinking partnership for the real problems: where are the leaks in your operation? (Is it pricing: have you actually calculated your overhead, or are you guessing? Is it structure: are you the bottleneck everything has to pass through? Is it leadership: are you so close to the standard that no one else can meet it? Is it brand and positioning: do you have the differentiation to charge what you actually need to charge?)
Most of these problems hard to spot from inside the thing. That's why you need someone outside it who can see the whole picture, ask the right questions, and think alongside you without any stake in the outcome.
I’ve got you.
What you get:
Two sessions a month to think out loud with someone who can actually keep up. No agenda required, just bring what's alive.
A thinking partner who moves between coaching, strategic observation, and visual thinking in a single conversation, depending on what the moment needs.
A shared document where you can drop questions, observations, and half-formed thoughts between sessions. Reviewed weekly. Not a hotline.
Pattern recognition that builds over time: the longer we work together, the better I can see what's yours versus what's just noise.
Honest challenge. I'm not here to agree with you. I'm here to think with you, which sometimes means pushing back.
Built-in flexibility. Session frequency can shift when life does, months can be paused when you need an integration period or I'm unavailable, and either of us can end the retainer with 30 days notice.
Not included:
One size fits all solutions
Conflation of your value as a human with the numbers in your bank account
“Work 24/7 and drive yourself into the ground” attitude.
You've built something (a practice, a firm, a business) and you're running it largely alone at the level that matters
You've done significant inner work and you’re no stranger to introspection. Maybe you’ve had a coach before
Success has made things more complex, not simpler, and nobody around you quite understands how that impacts you on the day to day.
You're the person everyone looks to for answers, and there's nobody above you to say 'good job'
The patterns that got you to where you are (excellence, DIY spirit, thoroughness, creative inspiration) are starting to cost you in your leadership, your relationships, your contracts, and your relationship to the work
You need someone to think about your business specifically, not hand you generic frameworks you've already read
You're making changes while still running the thing (in-flight repair) and you need someone who understands that context and can help you prioritize accordingly.
You want your coaching to go beyond mindset and address the system you’re building and living in.
Tend the Orchard is for you if:
How it works:
2 sessions per month, 60 minutes each. Ongoing, no defined end point
Coaching, strategic planning, and visual thinking in a single session. Whatever the moment calls for
Visual coaching sessions available at a retainer rate when you need something mapped
Shared async document: a running shared document where you can drop notes, questions, or reflections between sessions. Reviewed once a week (not a real-time inbox)
Pattern recognition across your work and leadership over time
Direct communication and honest challenge. This isn’t a space for comfortable agreement
Flexible: session frequency can adjust in a given month
Pause available: Months when Annalee is unavailable, or when you need an integration period, are scheduled with notice, and simply not charged
Cancel with 30 days notice, either party
Investment
400 CAD/month
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If you plan to be away or take time off from coaching let me know (with as much notice as you can) and we’ll pause your subscription until you are available to meet again. I will do the same when I take time away.
Sessions can be rescheduled with min 24hrs notice. Missed sessions with no notice will not be refunded.
How we get started
Before anything else, we have a conversation. A fit call… not a sales call. I want to know what you're working on, what's not working, and what you specifically need from a thinking partner. You'll get a sense of how I operate and whether this feels right.
If we're both a yes, I'll send you the retainer agreement and we'll set up your shared document. Your first session is usually a broad mapping conversation: where the business is, where the leaks are, what direction you’d like to head in. That session is the trail head for the journey.
Then, we meet twice a month. You bring what needs attention. I bring my best questions, pattern recognition, and honest push-back when it’s needed.
There's no defined end point. Some clients work with me for three months, some for years. The retainer is as long as it's useful, and you can pause or cancel with 30 days notice, no questions asked.
What if…
You had someone in your corner who already knows the terrain. Who you don't have to brief from scratch every time something comes up. Who can see the pattern in what feels like chaos, and help you find the lever worth pulling (without having any stake in which lever it is) and ultimately tie it all back in to the larger vision.
Imagine what it would feel like to think out loud with someone who can keep up, and draw out your best strategic thinking. And still be there next month to do it all again with the next thing.
“Annalee’s coaching has been invaluable as my firm has evolved over the years. She has supported me through everything from changes to leadership structure, business model, and moves; to smaller adjustments in management and operations. Her ability to come up to speed quickly and see complex patterns has saved us countless hours and wasted resources.”
-Austin H.
THIS WORK IS BUILT ON THIRTEEN YEARS OF WATCHING HOW ORGANIZATIONS ACTUALLY WORK.
I'm a certified coach with an executive coaching credential and thirteen years of experience running my own practice. I know what it feels like to be the one responsible for everything, to make decisions without a net, and to wonder if anyone outside the work can actually possibly understand your experience well enough to help.
My services include graphic recording and strategic planning facilitation; which means I've spent over a decade training myself to listen across complexity, find the patterns that the people inside a system can't see, and make the invisible visible. I’ve worked with everyone from businesses, to community organizations and governments. That's the skill I bring to this retainer. Not answers. A clearer picture of what you're actually dealing with, and better questions than you'd think to ask yourself.
I'm not going to tell you what to do. I'm going to help you see clearly enough to do what you do best.
FAQ:
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You’re the expert, I’m just organizing your best thinking. I don’t need to know all the ins and out of your particular business and expertise to spot the patterns. But where it does count, I’m a quick study.
As a graphic recorder, I spend a good chunk of my professional life in rooms full of experts speaking on a wide variety of subjects I know little about. I’ve refined the art of listening for what matters, and making connections quickly. And it turns out that highly specialized people benefit from seeing their ideas from an outside point of view. It fills a lot of gaps and blind spots.
In 2019 I was live drawing for a conference I was told was about women in STEM, but turned out to be PhD level presentations of research findings in molecular biology. Frankly, that’s been pretty hard to top on the overwhelm front. Do your worst. ;) -
Good! I don’t have one for you. Our work will be determined by what’s most pressing in your world, and what’s going on in the ecosystem that is your life and business.
The format is that we meet twice a month for coaching. It can be visual coaching or regular coaching, but it will always be responsive to what you need at that time. -
As your coach I won’t be giving you business advice like a lawyer, CFO, or another specialized consultant. I will ask questions, point out patterns I observe, and push back on assumptions to stretch your thinking. I’ll support you in doing what you do best. And I’ll point you towards those specialized consultants I mentioned when we’re getting in over our heads.
But, and it’s important to be clear about this: your decisions are yours. I’m not here to make decisions for you, and I don’t take any responsibility or assume any liability for the choices you make in your business. -
No problem! You are welcome to pause with notice any time or cancel with 30 days notice. No explanation needed. You can always come back if you feel the need further down the road.
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You’re the only one who can decide this, ultimately. There is a cost (to your business and to you personally) to proceeding without support, especially if you related to what’s written on this page. If I’m not the right fit, I hope you find the support you need. Whether that’s another coach or a specialized consultant like a marketing specialist or a financial advisor.
If you truly don’t have the cash flow for an investment like this you may not be at the point in your business where hiring a coach on retainer makes sense. If you’re just starting out and haven’t built a client base yet, the kitchen garden is likely a better fit. -
Wonderful news! I’m so excited for you!
If this is your first time working for yourself, or a brand new sort of business you’ve never explored, the Kitchen Garden is where you’ll find the kind of coaching you need.
If this isn’t your first rodeo, I can’t wait to help you translate and leverage everything you’ve learned from your past business experiences. Lets chat.
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Consultants provide specific deliverables and advice. For example, a structural engineer making sure your house design can withstand and earthquake, or a CFO for hire streamlining the money side of your business.
My role is general by design. I’m not here to provide a defined solution but to help you identify and define patterns, challenges and identify the solutions at a whole system level. My clients will then often hire specific consultants to help them implement a solution to a challenge we’ve identified together.For example, an operations consultant to implement scheduling and forecasting systems and software for a design + build company that was previously running on educated guess work. The coaching work was getting to the point where we could see the gap in the system that formed as the organization grew.
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Yes, but unlike the more classic forms of executive coaching we don’t stop at mindset and leadership. We look at strategic planning and your business and life as part of the same ecosystem.
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Visual coaching is like regular coaching + graphic recording-style sketch-noting. So you get a visual map of the conversation as a take away. You can read more about it here.
Tend the Orchard retainer clients can substitute a visual coaching session for a regular session whenever they choose. You simply select the visual coaching option when you book. -
As long as is useful to you. There’s no wrong way to do this.
I have some clients who’ve needed shorter sprints, and some who’ve been working with me for years.
You are welcome to pause or cancel your retainer and come back later.
When we spend this kind of time building a relationship, it becomes a valuable and precious thing. I feel like the door should stay open so you can access those benefits even if you feel like our ongoing work has completed it’s arc. I offer one-off stand alone sessions for former retainer clients who want to keep an occasional touch point. -
Either of us can cancel the retainer with 30 days notice. Any remaining unused prepaid sessions will be refunded, if applicable.
Sometimes we need an integration period or time off. We can absolutely pause your retainer for the time that you need. Same goes for when I’m away from the office.
If you can’t make it to your session you’re welcome to reschedule with 24hrs notice. Refunds will not be issued for ghosting or missed appointments without 24 notice (except in cases of truly exceptional circumstances).
Please take your time when deciding to work together. If you’re not sure if we’re a good fit I’m happy to meet for a vibe check call. You can book a free 20 min Q and A call here -
Access: I always ask my clients about their access needs and wants. Adaptation is the rule not the exception. We meet over zoom or over the phone and we can adapt that format in any way that feels best and that technology allows. Some adaptations include: camera off, fidgeting, doodling, shared whiteboard for brainstorming, pacing and moving about, laying down, automated subtitles and more. My goal is to make this a place to unmask.
Inclusion: I understand how important it is that the folks to whom we entrust our care honour and embrace our full humanity. That’s basic human decency. And so is being LGBTQ2S+ affirming, and respectful of the global majority (aka BIPOC folks). I am a white, disabled hetero, cis woman so naturally my default POV reflects that. But I’m always working to expand and challenge that POV and to learn. I can’t promise you perfect safety (no one can) but I can promise you a relational approach, humility and self-reflection.
