Dan Goodwin

The through-line

Everything Dan Goodwin says comes back to a single proposition: business owners get hurt by the questions they never asked. His formal training in interrogation and interview at the John Reed School in Chicago, the same school attended by "the feds, the stadies, the counties, the locals" [2], became a portable method rather than a job description. He does not want executives to become investigators. He wants them to "raise their awareness of those possible issues to develop and listen to their intuition when they have a gut shot feeling that something is wrong" [1]. He describes his own role as a sounding board and "the one that will ask the questions that aren't being answered right" [1], and frames the discipline as listening for absence, what psychology calls "leaning into negative space" where "you're listening more for what's not being said than for what's being said" [1].

The second half of the through-line is timing. Most of the work that reaches him arrives late, from clients he describes as having "their hair on fire" [1], and his stated preference runs the other way: "I would be rather working on proactive than reactive any day" [2]. His shorthand for this is direct. "My preference is that I talk to people before they need me. It's like dig the well before you need the water" [1], and when asked why a company should call, the answer is "the companies need to call me before they need me" [1].

On thinking like an investigator

The signature offering is a course he calls "how to think like an investigator and why you should" [1], and its content is closer to structured curiosity than to surveillance. He believes anyone can improve at research and interviewing by "creating a structured method to obtain information" [1], which combined with other observations lets owners and executive teams make better decisions [1][2]. The reality of the underlying craft, in his telling, is unglamorous: internal investigations covering fraud, theft, embezzlement, inappropriate relationships, IP violations and conflict of interest, work that was "all 5% James Bond and 95% documentation of said fun" [2].

The method he actually transfers is a baselining technique. Before any internal interview, whether the person was a suspect or a witness, he ran the same fourteen benchmark questions: full name, title, service date, supervisor. "These are automatic responses. I'm getting honest behavior, honest answers, automatic answers. And I'm watching you" [2]. The point is calibration, so that "later when we get into the heart of whatever issue that we were looking at, it was night and day to be able to spot the deceptive behaviors, the hymns and the haws" [2]. He is dismissive of folk cues, noting that everybody says people "look up and to the right. Not all the time, right? It's not like it is on TV" [2]. He also carries forward the mentor's line that became his mantra for investigative work: "Always prepare for the worst and hope for the best" [2]. For business owners, the translation is modest and achievable: ask thought-provoking questions and "listen carefully to the answers to see that there is alignment on values" [2].

On hiring, screening and the interview that was the high point

He agrees readily with the complaint that a new hire's "best performance was in the interview" [2], and says he has heard versions of that story repeatedly from companies in crisis and companies preparing for a transaction alike. His remedy is "better screening practices" [2]. He accepts that most people are genuinely aligned with a stated set of values, which is precisely why the exceptions are so costly: the tell is congruence between words and behaviour over time, not sincerity in the room. He also offers a technique lifted from interviewing and from sales, the golden silence, ask an open-ended question and then stop talking, "because they say in sales the first person that talks is the one that buys" [2].

On integrity, vision and why companies crumble

Asked to name the recurring failure patterns behind the reactive engagements, he starts with culture. The foundational issue is integrity, and specifically that owners must explain their values to employees and then behave consistently: "Their actions must be congruent with their words" [2]. The second cause of collapse is losing focus on the vision, a risk he ties to the founder pairing described in Gino Wickman's Rocket Fuel, where typically "one of those uh people is a visionary and one is an integrator" and a drift away from the shared vision "can cause a riff" [2]. He adds continuous learning and an overarching strategy as the remaining pillars, with strategy folding back into vision [2].

On the scale-up moment and the founder who will not let go

His sweet spot is companies "at a million" preparing to go "to five or ten or twenty" [1], and he is blunt about the structural weakness at that stage. These founders have usually bootstrapped and built the business from the ground up, and "if you insist on keeping control of every aspect of a business that is growing that quickly it can be a real challenge" [1]. They also lack the bench: no investigator on the payroll, maybe an HR person on site, an employment attorney on speed dial, but no set of advisers positioned to counsel them proactively, which is why "that reactivity can really be your own worst enemy" [1]. The engagement sequence he describes matches that diagnosis. In reaction mode you first stop the fire, "repair replace react retrain all the r words" [1], then run an assessment, then move into a transformative stage that makes sure the same issue cannot recur, whether that means shoring up security systems, IT security or HR training [1].

On people risk around a liquidity event

When ownership asks him to revet the management team before a sale, he reports that "80 to 90% of the time, the revetting of people and talent goes pretty smooth" [2]. What makes the exercise worth doing is his view of human behaviour under uncertainty. "Everybody has a secret. Everybody has secrets" [2], and a sale, transfer, merger or acquisition brings uncertainty, which "creates fear" and "creates doubt", so that someone who believes they can influence the outcome "may do something maybe out of character that they have never demonstrated before" [2]. The operative question is simple: "Do I have anybody I need to be worried about that is going to try to tank this deal for whatever reason?" [2]. His preferred mitigation is communication rather than surveillance. When people know what is going on and what is scheduled, "even if they don't like it", you gain "cooperation or at least acquiescence" as the process moves forward [2].

The other category of pre-deal exposure he flags is structural rather than personal: general partnerships never converted to C corps, S corps or LLCs [2]. He has lived through the consequences, where a general partner dies and, depending on how the paperwork was written, the surviving owners find themselves in business with a spouse and heirs who must be considered, and who will typically want "some sort of a check to go away" [2]. He is careful to say these are not really skeletons, they are "just life things that need to be addressed" [2], but the warning stands: "a business breakup, a business divorce can be worse than a personal divorce" [2], and the answer is direct, honest conversation that settles it all "before you go public with it" [2].

On delivering hard news

He opens client relationships by negotiating the terms of bad news, asking whether, on a scale of one to ten, they want to be tickled with a feather or hit with a nail-studded baseball bat [1]. He can do gentle, weaving the message in without hurting feelings, but he argues that route "may not be the most direct and profitable route surely is not the most timely" [1]. His preference is to inflict the pain quickly so the conversation can move to a solution [1]. The same directness runs through his favourite reality check: when an owner says they suspect someone is skimming and admits they first sensed trouble sixty or ninety days ago, his response is "go get a mirror look in it because now the person responsible for anything from 60 to 90 days till now is looking at you in the mirror" [1]. He accepts that this is a tough delivery, and attributes the gap to training rather than character, since most people "haven't been taught how to employ critical thinking" or how to hold crucial conversations and crucial confrontations to protect their assets [1]. The name of his firm makes the same point, CYA standing for cover your assets [1].

On emotion as the enemy of reasoning

He treats emotional regulation as a precondition of clear thinking rather than a separate wellness topic. He believes people need to address trauma and whatever has disempowered them, but argues that when the brain is full of adrenaline and cortisol from remembering an emotional event, that state "drives out your reasoning" and leaves you "in a constant state of feeling" that blocks the continuous process of critical thinking [1]. His prescription for clients is a sequence: acknowledge it, "name that feeling name that emotion", process it, attach meaning to it, and then move on [1]. He is explicit that the shortcut version fails, that it is "just not as easy as saying well you just need to move on", and that the work has to be done before the moving on [1].

On failure, relationships and the ripple effect

He is candid that his own record is not clean, including bad partnership choices where he "didn't follow my own advice sometimes and I got burned for it" [1]. From that he draws a circular account of judgement: success comes from good decisions, good decisions come from experience, and experience comes from bad decisions [1]. The practical conclusion is "fail as fast as you can and hopefully protect yourself as much as you can so that it's not catastrophic to your personal life or your business life" [1]. He applies the same lens to people, telling clients that "people come into your life for a reason a season or a lesson", where a reason may be short or long term, a season might be a joint venture or a fixed consulting engagement, and the lessons are often the most challenging [1]. Underlying it is a view of leverage that cuts both ways: "one chance meeting one relationship one incident can go up or down and can sink a company or can propel you to the highest levels of success" [1].

On where he shows up and why

He is deliberate about channel concentration. LinkedIn is "the playground that I play in the most like 98 of the time" because that is where business owners and leaders are, and where the people who need him most spend their time [1]. He has accounts on Facebook and Instagram, was an early Facebook adopter who reached 5,000 friends, and now rarely posts there, on the reasoning that he has to decide where his time earns the best return [1]. He uses the platform natively, sending video messages and making video introductions inside LinkedIn itself [1]. The tone of his posting is a technique, not a personality quirk: it is "a pattern interrupt", drawn from investigative school, where being "a little bit of a shock jock without offending anyone directly" makes the message memorable, and where the people who take offence "probably aren't a fit to work with me anyway" [1]. He offers a free thirty-minute intake with an open calendar four days a week, on the view that sometimes people already know the answer and "just need confirmation and affirmation that they're on the right path", which he treats as his gift back to the entrepreneurial community [1].

On family, stroke and leading with gratitude

Speaking about his father's major stroke six years ago and the mini strokes since, he insists on the systemic view: "it's just not that aaron had a stroke the whole family had a stroke" [1]. His stepmother has been the caretaker, and the distance between Kansas City and his father, roughly three hours, is a standing constraint managed with daily phone calls [1]. He deliberately starts with what survived, cognitive function intact, speech back to 100 percent, mobility back to 80 percent, saying "I always lead with gratitude" and "I always lead with what's thankful" [1]. He also describes an unexpected effect, that the stroke "has unlocked uh some stories in previous memories and childhood memories that I've never heard before", even as his father sometimes cannot recall yesterday's conversation [1]. He does not present the outcome as resolved, noting the ups, downs, blessings and continuing challenges as the family works toward quality of life [1].

Takeaways

• Ask before you need to: talk to an adviser while things are calm, because "dig the well before you need the water" beats arriving with your hair on fire [1].
• Build a baseline before you test for deception, using a fixed set of easy, factual questions to establish what honest, automatic behaviour looks like in that person [2].
• When you sensed something was wrong sixty or ninety days ago and did nothing, the responsible party is in the mirror [1].
• Culture failures trace to two roots: leaders whose actions are not congruent with their stated values, and founders who lose focus on the vision [2].
• Revet your management team before a liquidity event, because uncertainty makes people act out of character and a future buyer will run the same check anyway [2].
• Convert legacy business structures early; an unconverted general partnership plus a partner's death can put you in business with heirs at the worst possible moment [2].
• Process emotion deliberately, name it and attach meaning to it, because adrenaline and cortisol "drive out your reasoning" and block critical thinking [1].
• Agree with clients and colleagues in advance how they want hard news delivered, feather or nail-studded baseball bat, then deliver it fast so you can get to the solution [1].