Deliberate Leaders Podcast with Allison Dunn

By Allison DunnBusiness Entrepreneurship Marketing Management

Deliberate Leaders Podcast with Allison Dunn episodes

October 06The Cost of Not Thinking
The Cost of Not Thinking
“I’ll get to the strategic stuff when things calm down.”
It’s a familiar thought for business owners and leaders. But what if things aren’t calming down because there hasn’t been enough time spent thinking strategically in the first place?
In this episode, Allison Dunn introduces thinking debt, the ongoing cost created when important strategic questions remain unanswered.
Just like financial debt, thinking debt accumulates interest. Instead of dollars, leaders pay for it through repeated conversations, unnecessary decisions, constant interruptions, missed opportunities, and teams that remain dependent on them.
In this episode:
Why constant busyness can be a symptom of insufficient strategic thinking
What Allison means by “thinking debt”
How one unanswered pricing question created more than 60 conversations for a business owner
How two hours of focused thinking eliminated more than 50 reactive conversations
Why the most expensive cost of thinking debt may be the opportunities you never notice
How reactive leadership can unintentionally teach a team to stop bringing forward new ideas
The difference between responding to today's problems and spotting tomorrow's opportunities
The question every leader should ask about their own strategic thinking
A question to consider:
When was the last time you had a genuinely new strategic insight?
Not a solution to an urgent problem. Not a response to something that went wrong.
An opportunity, risk, or possibility you noticed before it became urgent.
If you’re struggling to remember, your attention may be consumed servicing thinking debt.
Coming Next
In the next episode, Allison shares the “payment plan”: a deliberate thinking practice that takes just 20 minutes a week, including how she used it to save five to six hours each week within the first month.
Think first. Lead deliberately.
Think First
6 min
September 22Built a Job, Not a Business
In this episode: Built a Job, Not a Business
A lot of business owners start their companies looking for freedom, only to discover that they’ve created a role they can never really step away from.
In this episode, Allison examines what it looks like when the owner becomes essential to nearly every part of the business and why that dependence can eventually limit both the leader and the company.
She explores the shift from doing the work to building the business, including the importance of identifying what truly requires the owner’s involvement and what should be delegated, systematized, or owned by someone else.
In this episode, you’ll hear about:
The difference between owning a business and creating a demanding job for yourself
How owner dependency shows up in everyday operations
Why being needed for every decision can become a bottleneck
The importance of separating what only you can do from work someone else can own
Why delegation requires more than simply handing off tasks
Building systems and clearer ownership so work doesn’t continually flow back to you
Developing a team that can think, solve problems, and make decisions
Moving from being at the center of the operation to leading a business that can function without your constant presence
The question to consider:
If you stepped away from your business, what would stop working?
The answer can reveal where you’ve built a business and where you may have simply built yourself a job.
Think First
11 min
September 15The Three Hours That Bought Back Two Years
The Three Hours That Bought Back Two Years
For two years, one executive Allison coached worked weekends just trying to keep up.
The problem wasn’t simply the amount of work on his plate. Every decision of real weight still came back to him. Even when work had been delegated, his team was waiting for him to approve, redirect, or make the final call.
The underlying issue was clarity: no one knew which decisions they actually had the authority to make.
In this episode of The Deliberate Leaders Podcast, Allison breaks down the three-hour exercise that changed that pattern and introduces a practical framework leaders can begin using with their teams immediately.
The Four Levels of Decision Authority
Level 1: Act
Make the decision and move forward. There’s no need to report back.
Level 2: Act and Inform
Make the decision and act on it, then let the leader know what you decided.
Level 3: Recommend
Research the options, develop a recommendation, and bring it forward so the decision can be made together.
Level 4: Escalate
Bring the relevant data and context to the leader, who makes the final call.
Allison also discusses:
Why delegating tasks without delegating decision rights keeps leaders stuck
How unclear authority creates unnecessary dependence on the leader
Why a decision problem may actually be a clarity problem
How to determine which decisions genuinely require your involvement
Why developing independent thinkers can initially feel slower
How to use questions instead of immediately providing answers
A practical script for changing the dynamic in your next one-on-one
How clearly communicating decision authority creates capacity for both the leader and the team
Try This This Week
For every decision someone brings you, pause before answering and ask:
Which level does this decision actually belong at?
Then say the level out loud when you hand the decision back.
The goal isn’t to remove yourself from every decision. It’s to become deliberate about which decisions actually require you and which ones your team is ready to own.
Think first. Lead deliberately.
Think First
11 min
September 08Thirty Hours a Week Making Decisions Your Team Could Make
In this episode, Allison explores what happens when too many decisions continue to land on the leader's desk.
When you're experienced, answering the question yourself often feels like the fastest option. But every time you immediately provide the solution, you may also be reinforcing a pattern: when something requires judgment, bring it to the leader.
Over time, that creates a team that can execute but still depends on you to think.
You'll hear about:
Why being the person with all the answers can quietly turn you into the bottleneck

How seemingly small decisions can consume a significant amount of a leader's time

The difference between delegating tasks and developing independent thinkers

Why answering quickly can create more dependency, even when you're trying to help

How to shift from solving the problem to helping your team think through it

Why asking the right question can be more valuable than immediately giving the right answer

How allowing people to own decisions builds judgment, confidence, and capability

What becomes possible for a leader when decisions begin happening at the right level of the organization
A question to consider:
How many decisions landed on your desk this week that someone on your team could have made?
The shift starts in the moment before you give the answer. Instead of automatically solving the problem, create enough space for the other person to think first. That repeated habit is part of the difference between a team that simply takes direction and one that learns to make decisions.
About Allison Dunn
Allison Dunn is the founder and CEO of Deliberate Directions and author of Think First. Through executive coaching, leadership development, and strategic planning, she helps leaders build stronger organizations and develop teams capable of thinking and leading beyond the person at the top.
Think First
8 min
September 013 Seconds Between You and a Better Decision
3 Seconds Between You and a Better Decision
This solo episode closes Allison Dunn’s series on the thinking traps that make smart leaders fail. She ties together the five traps from the series and shows why the real fix is not a new system or more willpower, but a tiny pause that interrupts autopilot.
The episode matters because it reframes leadership mistakes as habit plus speed, and gives listeners a simple way to catch themselves before reflex becomes a bad decision.
Key topics
In this episode, Allison Dunn explains why autopilot is the hidden force underneath the other thinking traps.

She shares a story about a CEO whose fast answers made him feel decisive, but whose team had learned to predict his responses instead of solving problems independently.

She defines autopilot as executing programs instead of making choices, and notes that the brain is wired for efficiency, not accuracy.

She describes a simple intervention she used after her own costly franchise mistake: a neon yellow post-it with the question, “Is this urgent or important?”

She explains how that one question created a three-second pause that helped her avoid bad hires, misused speaking opportunities, and unprepared client calls.

Allison connects the five traps in the series: autopilot, confirmation bias, recency bias, linear thinking, and validation seeking.

She argues that these traps compound into expensive mistakes that look like strategic decisions, creating motion without progress.

She frames better thinking as “cognitive compound interest,” where each improvement in judgment strengthens the next one.

She closes by asking listeners to identify their primary trap and choose one visible tripwire question to interrupt it.
Timestamps
(00:00) Why autopilot is the trap underneath all the others
(00:29) The CEO whose fast answers trained the team to stop thinking
(00:57) When predictable responses stop being real decisions
(01:27) Why the brain defaults to familiar patterns under pressure
(01:57) The post-it note that changed Alison’s decision-making
(02:26) Three seconds between stimulus and response
(02:56) The questions that become possible only after you pause
(03:25) How the five thinking traps compound inside a company
(03:54) Cognitive compound interest and why small shifts add up
(04:24) Judgment versus habit: what should actually run the company
(04:54) Naming your primary trap and choosing one tripwire question
(05:23) Final takeaways and the book Think First
Action Items:
Identify your primary thinking trap.

Pick one tripwire question that exposes it.

Put that question somewhere visible, such as a post-it, phone reminder, or meeting agenda.

Use the pause to ask whether the issue is urgent or important before responding.
Think First
6 min
August 25 The Answer You Already Had
Allison Dunn continues her series on the thinking traps that make smart leaders fail, focusing on validation seeking and why it can look like coachability while quietly eroding judgment. She shares a personal story about nearly buying an unnecessary financial platform and connects it to a larger pattern of outsourcing strategic thinking when you already have the context you need.
Validation seeking is a disguised trap
- It can look like humility, diligence, openness, and being well read, but still lead leaders to override their own informed judgment.
A personal near-miss with borrowed authority
- Allison describes nearly buying a financial analysis platform after a presenter implied she lacked the expertise to serve clients without it, despite having a finance degree and years of experience with business owners.
The expensive version of the trap
- She connects the same pattern to spending a quarter of a million dollars on a franchise formula partly to avoid trusting her own strategic thinking.
How the trap shows up in real life
- Searching for a template or business-in-a-box, consuming lots of content without turning it into strategy, and delaying decisions until an expert or peer group gives approval.
When outside input helps and when it harms
- Advice is valuable when it reveals a blind spot, but harmful when it replaces context-rich judgment with generic best practices.
Best practices are averages
- Allison argues that what works for other companies may be strategically wrong for your specific business, customers, and market.
The tripwire question
- Before seeking more advice, ask: “What do I already know to be true?”
Sort advice into two piles
- One pile reveals something you could not see; the other contradicts direct lived experience and should be treated skeptically.
Sometimes you are not buying information
- If you already know what the expert will say and consult them anyway, you may really be buying permission.
The cost of delayed decisions
- Waiting for validation can keep leaders from acting on what they already believe and know.
Timestamps
00:00 - What validation seeking is and why it hides in plain sight
00:29 - The near-miss investment that exposed the trap
00:58 - Why borrowed authority can override real expertise
01:27 - The expensive franchise example of outsourcing judgment
01:56 - How validation seeking shows up as template hunting and information overload
02:24 - Why outside input should inform judgment, not replace it
02:54 - Blind spot advice versus context blind advice
03:22 - The tripwire question: what do I already know to be true?
03:49 - Sorting advice into two piles
04:17 - When consulting an expert is really about buying permission
04:43 - The decision you are delaying because you want validation
05:12 - Next episode teaser: autopilot and the three seconds that separate reacting from leading
Think First
6 min
August 18When Adding More Makes Everything Worse
When Adding More Makes Everything Worse
Allison Dunn unpacks one of the five thinking traps that makes smart leaders fail: linear thinking. Using a real client example, she shows how adding people, tools, and process fixes can quietly create more complexity, lower profit per employee, and make growth feel harder over time. She also shares a practical question leaders can use to break the cycle and start solving the system instead of feeding the symptom.
Key topics
In this episode, Allison Dunn introduces the third trap in her series on the five thinking traps that make smart leaders fail: linear thinking.

She explains the “addition spiral,” where every new problem gets solved by adding more people, more tools, or more meetings.

A technology services client grew from 25 employees to 75 in three years and tripled revenue, but profit per employee dropped 40% and growth became increasingly painful.

The core issue was not growth itself, but the habit of responding to every breakdown with another hire or resource.

Allison contrasts addition with multiplication, noting that hiring feels tangible and immediate, while system improvements are less visible but create lasting leverage.

She identifies a hidden reason leaders stay stuck: addition makes them feel needed, while systems reduce dependency on them.

The key question she recommends is: “What would make this unnecessary?” instead of “How do we handle this demand?”

In the client example, unclear decision rights were causing communication breakdowns, and a simple decision framework took about three hours to create and eliminated most of the issue.

A lack of standard project approach caused coordination problems, and a few hours of system design and training removed the need for 15 positions.

The result was a 35% jump in profit per employee within six months.

Allison closes by encouraging leaders to review their last three resource additions and ask whether they were multiplication moves or symptom management.
Timestamps
00:00 - The thinking trap hiding inside your org chart
00:30 - How a fast-growing company became less efficient
00:59 - The addition spiral: more hires, more complexity
01:30 - Why linear thinking makes more input seem like the answer
01:58 - Why addition feels safer than building systems
02:28 - The uncomfortable reason leaders resist system fixes
02:57 - The question that breaks the spiral: what would make this unnecessary?
03:25 - How nine hours of systems thinking replaced 15 positions
03:53 - Turning resource requests into system-fix conversations
04:23 - A weekly check on your last three additions
04:52 - Where this sits in Allison’s book Think First and what comes next

Think First
6 min
August 11The Fire You've Put Out Repeatedly
Recognizing and Overcoming Recency Bias in Leadership
In this episode, Allison Dunn explores the often-overlooked trap of recency bias that can cause even smart leaders to focus on the most recent events rather than underlying issues. She shares personal stories, practical strategies, and questions to help leaders identify and break free from this pattern to make better decisions and solve problems effectively.

Key topics:
Definition of recency bias and its impact on leadership decision-making

How recency bias turns recurring problems into maintenance tasks rather than root cause solutions

Allison’s story of solving the same operational issue 14 times in six months and realizing it was a pattern

The importance of asking "Have I seen this pattern before?" before jumping into quick fixes

Distinguishing between solving symptoms versus addressing underlying causes

How firefighting creates a false sense of productivity and growth

Suggestions for leaders to identify patterns and escalate root causes within their teams

Introducing the mental model: "Solve at the Source" from Allison’s book Think First, Solve at the Source

Practical questions to challenge recency bias in daily leadership

The value of tracing problems to their source to save time and build sustainable solutions
Timestamps:
00:00 - Introducing the series on leadership thinking traps and why recency bias matters
00:28 - Allison shares her story of repeatedly handling the same operational fire
00:58 - How recency bias distorts perception of what’s urgent versus what’s important
01:26 - Examples of how leadership meetings focus on crises rather than strategic priorities
01:56 - The paradox of firefighting feeling productive but actually maintaining problems
02:25 - Practical question: "What is generating this problem in the first place?"
02:53 - Recognizing patterns by asking "Have I seen this before?" and avoiding symptom treatment
03:23 - How understanding problem patterns leads to faster, more sustainable fixes
03:53 - Encouraging teams to escalate root causes to reduce recurring emergencies
04:20 - Reflection question: What problems have you solved multiple times?
04:50 - Promoting the mindset of solving problems at their source and resources to help leaders
Think First
5 min
August 04The Case You Built After You Decided
Why Confirmation Bias Can Cost You Thousands — And How to Spot It
In this episode, Alison Dunn reveals how even the most experienced leaders fall prey to confirmation bias, often without realizing it. Through her personal story and practical advice, she shows how to identify and overcome this costly thinking trap before it causes irreversible damage.
Key Topics:
Alison shares her $250,000 mistake with a franchise purchase, illustrating how confirmation bias influences decision-making.

The subtle signs of confirmation bias in everyday leadership, such as defending decisions and dismissing conflicting evidence.

How to ask effective questions, like "What assumptions am I making?" and "What if those assumptions are wrong?" to challenge your thinking.

The importance of treating opposition or questions as gifts rather than threats to uncover hidden biases.

Strategies to prevent confirmation bias, including writing down assumptions and seeking genuine input before making decisions.

The role of self-awareness and curiosity in catching this trap early, especially in team discussions and strategic planning.

A teaser for the book "Think First" that offers five methods to detect and counteract thinking traps before they turn costly.
Timestamps:
00:00 - The high cost of decision-making mistakes leaders often mistake for good judgment
00:29 - Alison's personal story of buying a franchise with flawed thinking
00:59 - How confirmation bias creates case-building rather than genuine decision-making
01:29 - Recognizing confirmation bias: defense mechanisms and filtering evidence
01:58 - Everyday signs: sharing decisions after they’re made, seeking buy-in rather than input
02:13 - The importance of asking "What am I assuming?" before closing a decision
02:41 - Using questions to challenge assumptions and invite curiosity
03:07 - The difference between awareness and action: catching bias in real-time
03:37 - Practical questions to expose assumptions and invite challenge
04:07 - How to treat opposition and questions as gifts to avoid confirmation bias
04:37 - Final advice: reflect on whether you're still deciding or just building a case; unlearning bias
05:05 - Promotion for "Think First" and upcoming episode on solving recurring problems
Think First
6 min
July 28What Peers Actually Give You That Nobody Else Can
What Peers Actually Give You That Nobody Else Can
In this episode, Allison Dunn explores how leaders at high levels can overcome loneliness and information gaps by cultivating the right peer relationships. She emphasizes practical steps to build honest, context-rich connections that foster better decision-making and resilience.
Key Topics:
Differentiating peer groups from networking events, masterminds, or mentorship

The importance of lateral relationships at the same leadership level

How shared context accelerates honest and meaningful conversations

The significance of honesty without consequences in peer relationships

Learning to see outside the system through outside perspective

How peer reflection rewires leadership operating systems

Practical steps: conducting an honest relationship audit

The necessity of modeling vulnerability to enable open dialogue

Finding intentional communities that foster real thinking out loud

Building resilience by sharing burdens and embracing honesty
Timestamps:
00:00 - The real purpose of peer relationships at the executive level
00:30 - What peer groups are not and common misconceptions
01:26 - The power of shared context for high-quality conversations
02:23 - Honesty without consequences as a critical element
02:51 - Gaining outside perspective to identify blind spots
03:17 - How peer feedback influences decision quality
03:45 - The shift from loneliness to shared understanding
00:00 - The operating system update that peers can catalyze
00:24 - Conducting an honest audit to identify trustworthy peers
00:51 - Showing vulnerability to model honesty and open dialogue
01:19 - Seeking environments that foster honest thinking
01:48 - Closing tips: building resilient leadership through authentic peer relationships
02:09 - The impact of credible, honest peer support on leadership longevity
02:38 - The power of intentionality and honesty in navigating leadership challenges
03:08 - Promotion of the book "Think First" for strategic thinking habits
Resources & Links:
Think First by Allison Dunn

Deliberate Directions
Think First
8 min

About Deliberate Leaders Podcast with Allison Dunn

From the publisher's feed

Deliberate Leaders Podcast is dedicated to helping leaders build strong, thriving businesses. Join host Allison Dunn, executive business coach and owner of Deliberate Directions, as she spotlights today’s Deliberate Leaders who embrace the values of ownership, accountability, and reliability.

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