Anna O’Byrne

Anna O’Byrne is the principal at Captivate Content, Inc., a Toronto-area content marketing and copywriting service for small business. She is a seasoned content marketer, copy writer, management consultant, and facilitator.

Anna currently helps businesses:
Define Their Brand: Get crystal-clear on the essentials of branding, as a foundation for creating great content.
Develop Strategy: Decide where and how to amplify messaging to target the perfect customer.
Create Content: Craft captivating content for publication online and in print.

You can find Anna blogging on various topics at www.annaobyrneconsulting.com/blog. Contact Anna with questions on Essential Strategic Planning by sending an email to anna@annaobyrneconsulting.com.

Recent Posts

Why It's a Mistake to Run Strategy Sessions Yourself

Dec 1, 2015 by Anna O’Byrne in leadership & facilitation (3 minute read)

Small businesses thrive because their leaders have a can-do mentality; they take on all manner of specialist tasks, just to get it done on time and on budget. I'm the same.

But when it comes to running your strategic planning session, I'd urge you not to DIY.

You Really Do Need Neutrality

Anyone with a vested interest in the strategy shouldn't run the process. That's because when we have a vested interest, we tend to steer the process unconsciously. This applies to leaders and contributors, but when leaders facilitate, the influence is even stronger.

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Topics: leadership & facilitation

Strategic Planning for Remote Teams: Interview with Hubstaff’s Dave Nevogt

Oct 31, 2015 by Anna O’Byrne in leadership & facilitation (8 minute read)

Up today in the series on how remote teams do strategic planning: Dave Nevogt of Hubstaff on getting more freedom with strategic planning - starting with mission and values.

You’ll learn how Dave invested in a new approach to setting expectations and priorities, and how it sets him free from constant on-call management. We’ll also go a bit broader, and talk about vision, mission, values and goals for startups.

If you work remotely, you may know all about Hubstaff. Their content world is definitely sticky. It’s easy to stumble on a productivity post and stay for the full How to Manage University.

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Topics: leadership & facilitation

How a Completely Distributed Accounting Firm Does Strategic Planning, Virtually

Oct 21, 2015 by Anna O’Byrne in leadership & facilitation (9 minute read)

For the virtual strategic planning series I interviewed another expat entrepreneur living in nearly the same time zone. Carrie McKeegan and her husband, David, run their distributed business from Bali. Their company not only works virtually - with a global team - but exists to solve a pain point inherent in working abroad: tax complications.

The McKeegans came to appreciate the expense and challenge of expat taxes while working as Americans in the UK. “While they both loved being American and living abroad, they were fed up with the process of filing US expat taxes.” In 2008 Carrie and David founded Greenback Expat Tax Services.

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Topics: leadership & facilitation

Strategic Planning with Remote Teams Part 5: Goals & Strategies

Oct 13, 2015 by Anna O’Byrne in remote work, meeting design (3 minute read)

Once you have an established vision and mission, it's time to figure out exactly what you'll do to achieve them. The Complete Toolkit for Strategic Planning with Remote Teams breaks this work into two sessions. In the first, the team establishes a series of high-level goals, and in the second, they define the specific strategies they'll employ to achieve these goals.

The information that follows is an excerpt from Anna O'Byrne's detailed Guide that accompanies these templates.


How Goals & Strategies Fit in the Essential Strategic Plan

The Essential Strategic Plan is concerned with what you want to achieve – your "ends" – and how you’ll attain these ends, at a high-level. The "essentials" covered in this series of meetings make up the core of your strategic direction.

  • The vision, mission and values define your organizational identity; your very brand. They become the filter through which you evaluate new opportunities, and can drive day-to-day decisions.
  • Goals and strategies define where you’ll focus energy and resources.
When complete, the Essential Strategic Guide prints out on one or two pages.

True to its name, the Essential Strategic Plan covers the basics; a minimal but fully functional strategic plan. Depending on your organization, you may wish to plan to a finer level of detail. For example, you might break down broad strategies into more discrete tactics. Tactics are actionable steps towards achieving your goals. You can also break down goals into specific, measurable objectives. Then, as you define measures, you can capture these in a scorecard to monitor your progress.

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Topics: remote work, meeting design

Strategic Planning with Remote Teams Part 3: Crafting the Vision and Mission Statements

Sep 22, 2015 by Anna O’Byrne in leadership & facilitation, remote work, meeting design (6 minute read)

This post is the third in a series. You can find the whole series in our Complete Toolkit for Strategic Planning with Remote Teams.


Have you ever tried strategic planning without first getting your vision and mission right? What did you find?

If you were a small, cohesive group, maybe you breezed through goal-setting based on complete unity. It happens, but it’s rare.

For everyone else, here’s what typically happens:

  • You generate ho hum goals: goals that just don’t stretch the team.
  • It sometimes feels like you’re writing a to-do list, rather than a strategic plan.
  • You sign-on for strategies that are far-removed from what you see as your core business.

In short, strategic planning takes far too long and feels anything but strategic. You look at the end result and fear you’ve created a Frankenstein: pieces from here, pieces from there, with no final coherence.

And the challenges don’t end at strategy. Teams that operate without vision and mission feel the effects everywhere.

How? Here are some everyday signs you need a vision and mission:

  • Your branding feels disjointed or superficial.
  • People outside don’t get what you’re all about.
  • People inside don’t see their work as meaningful.
  • You zig and zag to meet opportunity, but you get no closer to your dream.

If a vision and mission are this important, why would anyone skip it?

First, we’re all pressed for time. Vision and mission sometimes feel like the extras we’ll get to when we have space to breathe...or when we hold our next retreat.

Second, we make assumptions. Many teams believe they’re on the same page when it comes to where they’re going, but when they sit down to plan strategically, the gaps become glaringly evident.

Finally, we misunderstand the value of having relevant, vivid, fully thought out vision and mission statements.

Let me clarify.

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Topics: leadership & facilitation, remote work, meeting design