What It Means To Engage With An Advisor

People often wonder what makes advising actually work. It's a good question.

It does feel nebulous because the business is moving and the pressures are very real. Add to that the sessions are the delivery… and of course we’re scratching our heads. I mean, how many people even know exactly what advising is? 

I’ve noticed consistently that clients who engage fully in advising tend to experience similar shifts over time: more clear decision making, reduced load, stronger boundaries, and more sustainable momentum.

When leaders engage in advising, early relief is very common. The thing that’s not usually expected is the ebb and flow that follows, and the recalibrations that happen over time. It’s the whole process that brings and solidifies the shifts. 

Let’s walk through what that actually looks like.

I know we’re all sick of the double negative followed by a positive that genAI can’t help but sneak in - I am choosing to use one purposefully here. Working with an advisor is not about being perfect or becoming endlessly motivated. And it is not about pushing through discomfort to just “do the work”. 

Engaging fully is very much a practice. Active participation determines how much you get out of it. Especially when working on untangling things.

In this article, I want to share what I see making the biggest difference. I will come in and update this as time moves forward and I learn more. Because the ongoing practice goes both ways. In my opinion, that’s the most important thing to look at when you are vetting any type of support or vendor. 

First: what engaging fully is not

*I know! “This is not… this is not… because it ACTUALLY IS…” again, I promise I am the human Jamie typing & editing & articulating this 😉

Engaging fully in advising does not mean:

• Always feeling clear or confident

• Having the “right” questions ready

• Moving quickly or showing constant progress

• Agreeing with everything I reflect or name

• Feeling good in every session

You see why I’m including the “this is not…” here? There is almost always a pressure to perform. I want to start here because it’s a huge barrier to getting the support you deserve. And whether that’s with me or not, this is a barrier for all of us. 

I’ve had so many clients talk about not looking into what they need or delaying reaching out. The most common reason is that they felt the weight of it all. Needing to show up at full capacity feels like too much. Here’s a resource (5-10 minutes) that can help you see where your capacity is strained and which types of support might best serve you. Because I’d bet that adding one more heavy pressure is not what you need right now. 

Here’s the reality that’s hard to see when you’re already carrying too much… If advising required leaders to show up as their absolute best selves, it would only be for people who have the mental energy and don’t need it. (Don’t you love when logic feels like walking into a sliding glass door?!)

Another common misconception is that advising sessions require outsourcing your decision-making. This is not at all what advising is or should be. Independent advisors do not give you direction. We are here to offer you support and insight fueled by decades of experience. We are not in every meeting, nor do we know all the things you are considering and weighing and balancing. 

Advising is not handing over authority. 

Having an advisor helps you build a practice that strengthens your capacity - through bringing a fresh perspective with relevant insights and being your sounding board. Over time, this practice naturally increases your ability to hold it all (and often, it also shifts how priorities are made and how the work gains and sustains momentum without burning you out). Thus…

What engaging does look like 

Without sounding too nebulous… the practice is in staying present and communicating. It sounds simple. It is not. Not at all, not for any human. It’s so much easier to rush through and… I don’t need to explain it. We all do it ;) 

Thankfully practice means that things will ebb and flow. Work and life pile up and so we check in with your energy and where you’re at that day. What you need from the session. I can bring what we spoke about last time, I’ll hold threads, you’ll bring the things that are weighing on you most. And it really does all balance out. That is the rhythm. 

And because of the sway, advisors help redirect when it’s called for. We give you slack when needed. We name patterns if they emerge, so you get a snapshot of the things you can’t see from the inside. 

Knowing how I work, and how advising leaders whose businesses are in the early stages often goes… These are the things my clients bring up when we are checking in about how our work is going. Discussing what the impact has been and what’s opened up (the flow). And when we look back on the times that were harder (the ebbs).

I hope this helps anyone who is considering advising and is curious what it will take to get the most out of it. 

1. Staying present when the work stops feeling clean

Early sessions are often energizing. There’s relief in being seen and having space to think.

And as that integrates into your daily work, naturally certain plates get into balance and other ones need attention. A perfect analogy.

Competing priorities. Emotional weight. Old patterns. Resistance. Fatigue. Second-guessing.

Engaging fully means not disappearing when that happens.

So instead of pushing through or forcing clarity, it means staying in the room. Naming what’s harder, slower, or more confusing. What's challenging about this is the automatic inclination that tells us we need to jump to distraction, urgency, or avoidance.

This is where advising actually becomes useful. Sitting in the discomfort of it, and choosing the direction you take from a grounded place.

2. You’re willing to slow down without collapsing

There are moments in advising where the most responsible move is to slow the pace because too much is happening at once. Again, it feels very counterintuitive at first.

Engaging fully means being willing to pause long enough to:

• notice what’s real

• separate signal from noise

• feel where decisions are getting stuck

This is capacity-building.

Slowing down here feels like it means losing momentum. Ironically, this is what actually prevents false momentum that later crashes or stalls and has to be unwound.

3. You let boundaries clarify the work instead of fighting them

Advising requires boundaries to stay ethical and effective.

Sometimes that means:

• naming when the work is drifting

• redirecting away from therapy territory

• slowing down a push toward premature action

• distinguishing emotional processing from strategic decision-making

Engaging fully doesn’t mean liking those moments. It means not trying to override or negotiate them away.

Boundaries aren’t about rigidity. They’re what make trust, progress, and sustainability possible over time.

4. You take responsibility for integration between sessions

Advising doesn’t work if everything lives inside the hour.

Engaging fully means:

• sitting with what surfaced after we meet

• noticing where it shows up in real decisions

• trying things, even imperfectly

• observing what happens and bringing that back

This doesn’t require flawless execution. It requires relationship with the work between sessions - not treating advising like something that happens to you, but something you’re actively in.

5. You stay in ownership, especially when it’s uncomfortable

There are moments where clarity asks for something inconvenient:

• a harder conversation

• a decision you’ve been avoiding

• letting go of an identity that no longer fits

• accepting a capacity limit instead of pushing past it

Engaging fully means staying in ownership here. Not looking for someone to decide for you is so much harder than it sounds! It can be so easy to accidentally turn discomfort into justification, blame, or paralysis.

Advising supports you through those moments. It can't bypass them for you (unfortunately!)

About ebb, momentum, and expectations

One important thing to name clearly:

Many clients experience early relief and renewed momentum in the first few sessions. That’s real.

It’s also not the whole story.

Over time, periods of ebb, resistance, and recalibration are normal. They aren’t signs the work isn’t working — they’re signs you’re building something more durable than short-term relief.

Engaging fully means understanding that leadership capacity grows through those phases, not around them.

A gentle but honest boundary

Advising works best for people who want partnership, not rescue. And remember that every advisor is still a human. We all have our own approach and perspective. Finding the right match for you is key! 

If you’re looking for someone to:

• take over decisions

• tell you what to do

• make discomfort go away

There are other forms of support that may be a better fit - and that’s absolutely okay. Sometimes things are too much and it’s not the moment to try and stretch. Other times, when things are too much, having dedicated time to bring perspective to the work helps lighten the load so that you can rebalance. It’s different for everyone, and it will change over time. This is life. 

My approach is to offer steady, grounded partnership that helps my clients think more clearly, lead responsibly, and build a business they can actually stay with.

Engaging fully means meeting that partnership with presence, ownership, and honesty, across the ebbs and the flows. 

A closing thought

You don’t need to be ready in every way to engage fully in advising.

You do need to be ready to:

• stay when things get complex

• let clarity take time

• hold your leadership rather than hand it off

If that resonates, advising can be a powerful container for growth.

If it doesn’t, that’s really useful information! Because leaders need all kinds of people and practices in their support circle. There is no judgment about what specifically is needed. Not from my POV. 

Knowing what will be right for you before you commit is also a part of what engaging fully looks like.

Take your time, only you know what is right for you.