Which Leadership Support Option Is Best (and when)

You likely have a sense of where things are strained but it can be hard to see from the inside. If you’re wondering what types of support go with which common business constraints, and what that actually means in practice, you’re in the right place. 

This article is your introduction (read on!)

Here's the quick assessment that helps you see where you're most strained.

And here's the article that helps you interpret your results without relying on me or paying for someone to tell you what you can assess yourself.

The goal of this resource is not to steer you toward a particular service.

It’s to help you understand your landscape well enough to make an aligned choice. Whether that means seeking support from me or not… I want this to help you understand your options and decide which areas would be good to explore. 

Support works best when it matches the actual needs and constraints, not the loudest pressure or the most common advice. 

If you reach out, I’m happy to share my perspective or discuss your results! 

But this resource is intentionally complete on its own. Clarity shouldn’t be gatekept.

Okay, let’s dive in! 

The five domains we need to look at are:

1. Decision clarity 

2. Structural strain 

3. Capacity & energy 

4. Execution & ownership

5. Readiness

By seeing which section or sections are showing up most for you, we can start to see what support options will best address those. 

The options this will illuminate for you are:

1. Advising / Thought Partnership

Potentially useful when the primary constraint is:

• decision clarity

• orientation

• leadership sensemaking

• separating signal from noise

• leadership capacity or skill building

Keep in mind there are different approaches to advising:

• strategic

• leadership development

• reflective / sensemaking or thought partnership

• financial

• operational

• executive coaching

• HR & organizational development

• technology & IT

• sales & business development

• risk management & compliance

And even within these, there is a range of styles. It’s key that you find the type and style that fits best with what you need and how you work.

2. Consulting

May be helpful when the primary constraint is:

• structural strain

• systems that haven’t caught up to growth

• org design, workflows, roles, operating models

• change management

• execution within a very specific and highly-specialized specialty

Consulting spans many many specialties. For this assessment, the most common types are going to be:

• ops consulting

• org / system design

• embedded or project-based consulting

Note:

I don't offer consulting unless it's with a client I'm currently advising. Here's why!

The assessment will help clarify when consulting should come after orientation vs before hiring. Timing matters as much as type when it comes to what will help you most. 

And please, always feel free to book a chat with me during my office hours (no cost, just sharing insights).

3. Hiring & Execution Support

This is for when the primary constraint is:

• execution strain

• ownership & responsibility growth

• follow-through bottlenecks

• load that should not be held by the founder anymore

This support includes things like:

• full-time hires

• part-time or fractional roles

• Independent contractors, vendors, or agency support

• internal delegation and redistribution (always the first thing I'd recommend looking at with fresh eyes)

This is not about scaling. It’s looking at appropriate ownership and resourcing.

4. Relief, Containment, or Stabilization

This is for when the primary constraint is:

• capacity

• energy

• sustainability

• nervous-system overload (without pathologizing)

Support here includes:

• reducing scope

• redistributing load

• pausing strategic work

• choosing not to add support yet

It doesn’t always feel like it, but this is a very valid (and often responsible) choice.

5. Waiting / Not Engaging 

This part is so important. Sometimes once you’ve decided to explore what kind of support you might want, it starts to feel like you must choose one. That’s simply not true!

This option helps us see when:

• engagement itself would add pressure when you don’t have the space for it

• reflection isn’t accessible (we’re all human, this happens and is valid)

• clarity would be forced instead of earned (this is the most common reason people push through)

This is about timing. That’s it! And as with the previous section, it is a valid and often responsible choice to pause or address the issue internally. 

What the assessment intentionally does not cover

• Coaching as motivation or performance fixing

• Productivity hacks

• Therapy or emotional processing

• “One-size-fits-all” flattening

• Sales-led service matching

I don’t find those useful so I do not recommend them. That is my personal and professional lens, it does not mean these things aren’t right for some. They just do not fit for me. So I don’t include them in my resources. 

Okay, if you read this far. Here’s where you take your assessment and then hop to assess your results. I really hope this helps you see things more clearly so you can find the most aligned support possible!