Bespoke Solutions

🚨 The Reposted Job Dilemma: Why Your Chief of Staff Role Remains Unfilled—and What It’s Costing You It’s a pattern I see far too often: a company posts a Chief of Staff role, receives hundreds of applications, but doesn’t move forward with anyone. A month or two later, the role is reposted…and reposted again. Here’s the hard truth: Every day this role remains vacant, your company is losing momentum, raising red flags to qualified candidates, and burning out your team. 🔥 The Role is Critical—But Still Unfilled A Chief of Staff isn’t a “nice-to-have”—it’s the force multiplier your leadership team needs to execute strategy, align cross-functional teams, and accelerate growth. Letting this position linger unfilled signals misalignment, wasted time, and missed opportunities. 🔥 Diminishing Returns on Talent The best candidates—the ones ready to hit the ground running—apply early. They’ve already envisioned making a significant impact at your company. But if they’re met with silence or indecision, they move on. By the third or fourth repost, these high-caliber professionals are no longer in your candidate pool—and may even view your repeated posting as a red flag. Chiefs of Staff are corporate smoke jumpers—thriving on diving into firestorms, extinguishing chaos, and delivering solutions. If your company can afford to wait multiple financial quarters, reposting the role over and over, you send an unintended signal: either the problems aren’t urgent, they’ve been allowed to fester too long, or worse—you don’t truly know what you’re looking for. 🔥 The Talent Acquisition Hamster Wheel Each repost isn’t just a drain on your timeline—it’s a drain on your Talent Acquisition (TA) team. They’ve already poured over resumes, screened candidates, and thoughtfully submitted top-tier recommendations. When no one is selected—not once, but twice or even three times—they begin to lose energy and trust in the process. TA teams start questioning the guidance they’re receiving from the executive team: If no one is ever the “right” fit, why try? If the ELT is looking for something hyper-specific, why isn’t the job posting more reflective of those needs? The hamster wheel spins on, and your TA team loses focus and momentum just when you need them most. 🔥 The Underlying Issue: Misalignment Here’s the real challenge: Chief of Staff roles are nuanced. Strategic visionary? Operational tactician? Both? Leadership teams often aren’t fully aligned on what they need, creating bottlenecks in hiring. Meanwhile, your organization operates without the leverage and focus this critical role provides. 💡 Bespoke’s Fractional Chief of Staff Solution: Stop spinning your wheels. At Bespoke Consulting, we cut through the noise to provide immediate, high-impact support with our Fractional Chief of Staff services. Reach out to me at Bespoke. Let's make sure you get it right. #Leadership #ChiefOfStaff #FractionalSupport #BespokeConsulting #MoveFaster #OperationalExcellence

Three Questions You’re Not Asking - BUT MUST - When Hiring a Chief of Staff As an addendum to this post from Bespoke, many TA and HR professionals miss the mark of hiring the right Chief of Staff by failing to ask questions that reveal the unique skill set this role demands. A Chief of Staff isn’t just another executive—they’re an organizational chameleon who must navigate ambiguity, influence without authority, and ensure smooth execution of your vision. Here are three game-changing questions you should be asking to find the right candidate: 1) Can you share a time when you faced a time-critical problem outside your department or expertise? How did you handle it? Why this matters: Chiefs of Staff are constantly thrown into situations where they lack expertise or direct authority. This question isn’t about the specifics of the problem or even whether they succeeded. It’s about uncovering how they approach challenges outside their comfort zone. Look for someone who: -Demonstrates curiosity and learns quickly. -Leverages relationships with colleagues for insights and support. -Can think critically and resourcefully when navigating uncharted territory. -This is the kind of candidate who will step up to tackle unexpected issues without relying on surface-level solutions. 2) Who is the most senior person you’ve acted as a proxy for, and in what capacity? How did you prepare, and what did you contribute? Why this matters: Acting as a proxy requires poise, judgment, and the ability to command respect. Whether they represented a VP or the CEO, the focus here is on their preparation, confidence, and ability to deliver in high-stakes moments. The right candidate will: -Unde

Why CEOs Keep Hiring the Wrong Chiefs of Staff In recent weeks, I’ve spoken with numerous Talent Acquisition professionals, Presidents, and CEOs about their need to hire a Chief of Staff. For many leaders outside of government, this role is novel and often misunderstood. In my former career at the CIA, Chiefs of Staff were integral—trusted problem solvers who enabled leaders to think strategically while translating vision into action. The potential of the role often excites executives. They imagine hiring someone who embodies extraordinary soft skills—strategic thinking, emotional intelligence, adaptability—and can serve as a behind-the-scenes force multiplier. Someone who can: - Turn strategy into action. - Build and nurture relationships. - Foster collaboration across leadership. - Run strategic programs and projects. - Design and manage company-wide initiatives, like OKRs. - Act as the CEO’s proxy. Represent their vision when they can’t be in the room. What they’re really looking for is a corporate athlete: someone versatile enough to tackle any challenge, bridge gaps, and solve problems across domains. And yet, during the hiring process, many executives lose sight of this vision. Instead of seeking the broadly skilled, adaptive leader they initially imagined, they pivot to hiring someone hyper-focused on solving their most immediate pain point. Is it a marketing pipeline issue? Suddenly, they’re looking for a marketing expert. Sales underperforming? They’ll zero in on someone with revenue ops experience. Customer Success too costly? Time to find someone with a track record in support operations. Here’s the problem: today’s most pressing challenge is not tomorrow’s. This myopic approach—hiring for a specific function rather than adaptability—leads to short-term gains but leaves the company vulnerable when the inevitable novel next issue arises. Even worse, when the new hire fails to handle issues outside their specific expertise, CEOs often conclude, “Chiefs of Staff are useless—I won’t hire another.” The best Chiefs of Staff aren’t defined by depth in one domain; they’re defined by their ability to operate across domains. They connect dots, anticipate challenges, and respond dynamically to the CEO’s evolving needs. That’s why the role has long been a cornerstone in government and high-stakes environments—it requires someone who can parachute into any problem and deliver results. The question leaders should ask isn’t “Who can solve my current problem?” but “Who can I trust with ANY problem?” The Chief of Staff you need builds processes, relationships, and strategic frameworks to tackle not just this quarter’s crisis but the unpredictable challenges ahead. Hiring otherwise doesn’t just shortchange the role—it shortchanges the organization. Reach out to me at Bespoke. Let's make sure you get it right.

It is with the utmost pride that I want to announce the Keystone/Boys and Girls Club team I mentored and coached through their SCI pitch is bringing their plan to fruition in just 2 months! If you are in or near Woburn, MA this Saturday, June 8th from 1-4p, come down and see what outlets your community has to offer you of which you may not have been aware! On a personal note, I have had the unique privilege of watching these young men and women bring this program from ideation to completion. I've taken a personal interest in mentorship and leadership and have been around the block. I can say that these young talented high school standouts' drive, professionalism, and entrepreneurship stand up to the officers I led and mentored for a decade with the CIA's National Clandestine Service and the dozens of CEOs I've coached and consulted for over the last 7 years. Both Bespoke Solutions and I are proud to have played a small part in their accomplishment!

Leaders need to prep for failure because it is a very real threat. If Eisenhower did it for the D-Day invasion, you can do it too. I have been speaking with some CEOs recently about the fact they see their leadership as a critical factor for a project’s success, but ascribe externalities (and omit their leadership) to the causes for their companies’ obstacles and failures. Why? Because poor leaders refuse to accept blame. A leader not taking responsibility for their poor decisions is simply a lack of leadership. Yes, market timing, inflation, lending bottlenecks, etc can be pointed at when a launch goes wrong, but the lack of those same obstacles aren’t referenced when a launch goes right…it’s “I was at the helm and I conquered all.” Thinking about the need to accept failure as a very real outcome, and one’s own leadership as the cause, got me to thinking of the little known unsent Eisenhower letter to President Roosevelt wherein he informs the President that D-Day has failed and it not his men’s fault but his own. If the leader tasked with the liberation of Europe, the end of Nazi tyranny, and the return of democracy can anticipate failure and accept the responsibility for that failure, you, CEO, can stand before your board with your back straight, shoulders back, and state (with the same power and confidence you would have embodied in success) that it was your decisions that lead to an unsuccessful outcome. Own your failures so you can learn from them. Never be afraid to fail but never be willing fail the same way twice! This is a letter worth reading and I’ve provided below. For background check out the National Archived link here: https://lnkd.in/erGy2hGZ

Apologies for the delay in posting! With baby #2 due this week, I've been been the GC renovating 3 rooms of our home over the last month. Without further ado: The Importance of a Well-Rounded Chief of Staff in Mitigating the Pitfalls of the Peter Principle for Startup CEOs As a seasoned change management consultant, I've navigated through the intricacies of organizational dynamics and witnessed firsthand the consequences of the Peter Principle, especially within the realm of startup companies. The Peter Principle states that individuals are generally promoted to positions beyond their competence, ultimately resulting in organizational inefficiencies and failures. Nowhere is this phenomenon more evident than in the realm of startup Founder/CEOs, who often find themselves thrust into the highest echelons of leadership on little notice and told to deliver. On Monday she could be coding with three friends since high school, by Tuesday could get VC capital, and by Wednesday be the CEO of a company valued in the millions of dollars and tasked to ramp-up to profitability over six quarters. Few Founder/CEOs survive this transition because they feel drawn to stay close to their product/team working in the trenches. This is the crux of the Founder/CEO befalling the Peter Principle - they are great coders but choose not to be great at managing coders. So, how can they overcome this pitfall? Enter the Chief of Staff – a critical ally in the arsenal of a young startup CEO to avoid the Peter Principle trappings. Unlike traditional executive roles, the CoS operates as a versatile linchpin, bridging the gap between strategy and execution. The COS does this by standing outside of the standard COO/CTO/CRO hierarchy and instead focusing on giving their CEO the three things they don't have enough of: (1) TIME to think strategically (2) BANDWIDTH to explore options and peek 1/3/5 years down the road and (3) COMMUNICATION STRUCTURE to cascade her decisions down the corporate ladder. How does the CoS do this? By: (1) overseeing day-to-day operations (2) being a trusted advisor and proxy when needed (3) handling ad hoc issues across all departments of the company (4) creating strategic initiatives and navigating complex challenges (5) acting as a sounding board and providing critical feedback/guidance every step of the way (6) streamlining operations, aligning priorities, and driving execution across the organization (7) keeping their finger on the pulse of the company. When looking for a CoS, remember their role is to help you rise above the day to day operations of HR, Legal, Marketing, Ops, Accounting, PR, etc.. As such, your candidate's work experience should reflect that breadth. Make sure to look beyond just MBAs. You're not looking for a master of one or two issues - as MBAs often are - rather, you're looking for a diversified corporate athlete capable of deftly handling anything.

Terminal Leadership: The Courageous Act of Stepping Down/Away to Better the Mission In the wake of the crisis facing the Biden campaign after the Special Council's report, the concept of Terminal Leadership, where a leader steps down for the greater good of the mission, becomes a pertinent consideration. Effective leadership demands the ability to recognize when a leader's mandate has waned, and the team's respect has diminished. Despite the prevailing notion of leadership emphasizing resilience, there are instances when a leader must courageously step down to preserve the mission and the organization. A leader's effectiveness hinges on maintaining a connection with those they lead, going beyond mere authority to earn and retain trust, respect, and support. Severing this connection, whether through misguided decisions or a failure to adapt, requires a leader to assess their ability to steer the ship effectively. Equally crucial for sustained effectiveness is the respect a leader garners from their team. Earned through consistent and ethical decision-making, effective communication, and genuine concern for the team's well-being, lost respect becomes a significant impediment to mission achievement. A leader clinging to power despite a decline in respect risks damaging not only personal reputation but also the cohesion and morale of the entire organization. When a leader finds themselves in a position where the mandate and respect of the team are diminishing, the ethical course of action is to step down. This act of humility is not a sign of weakness but an embodiment of leadership integrity. Recognizing the need for change and making room for new leadership paves the way for fresh perspectives, renewed motivation, and the revitalization of the organization's mission. In the end, the concept of Terminal Leadership is not a theoretical consideration but a crucial aspect of effective leadership. Leaders must have the courage to step down gracefully when the essential components of mandate and respect are slipping away. This act, rooted in self-awareness and humility, serves as a testament to leadership integrity and is a vital step toward ensuring the ongoing success of the organization's mission.

BespokePost 2 - A CEO needs to know his/her leadership style and engage a complimentary C-suite to address crises. The ability of a CEO to effectively manage crises is pivotal for the survival and triumph of any organization. This is especially true for early-stage companies, including seed stage to Series B startups. Founder CEOs, often constrained by capital considerations, find themselves navigating the delicate balance of running lean operations. As a consultant, investment banker, and former spy, I've been at the speartip of many crises. I find crisis has a way of sifting leadership styles into three major categories and always underscores the need to adeptly curate a C-suite accordingly. (Note: I’ve included fail vice success examples because there are too many factors to pin a success on leadership - market timing, cultural zeitgeist, etc. - but failures can easily be tied to leadership…and these CEOs and C-suites were the source of failure here). (1) Autocratic Leaders: In a crisis, autocratic leaders take charge quickly and make decisions decisively. This can be effective in situations where rapid, clear direction is needed, or where there is significant public pressure to address an issue. However, these "timely" decisions are often made based on a ratio of gut instinct and incomplete data that result in complete misfires and/or future significant "aftershock" mini-crises. Fail example = Travis Kalanick (Former CEO of Uber) - Unilaterally drove the deception campaign in response to USG investigations of Uber's Greyball tool. RESULT - FIRED (2) Democratic Leaders: In a crisis, democratic leaders take more time to gather input. While this can lead to well-rounded decisions that fully address an issue, they often prevent the application of a quickly- deployed 80% good-enough response over a protracted period of PR echo-chamber-like hell. Fail Example = Bob Chapek (Former CEO of Disney) - C-suite crowd-sourced his reaction to the "Don't Say Gay" legislation delaying his public response. RESULT - FIRED (3) Laissez-Faire Leaders: In a crisis, laissez-faire leaders provide little or no clear direction so their highly-capable subordinate teams can work the problem without independently. This style can be effective if the team is highly skilled and there is little public scrutiny, but may be detrimental in situations wherein public relations require a public-facing CEO to appear to be (if not in reality) hands-on. Fail Example = Tony Hayward, (former CEO of BP) utilized a hands-off approach, deferring action to his subordinates during the Deepwater Horizon oil spill. RESULT - FIRED Ultimately, each leadership style has its strengths and weaknesses. CEOs must understand their style of leadreship and select individuals for their C-suite who complement their strengths and augment any weaknesses. This is what we do! Give us a call to ensure your leadership team is adeptly aligned for effective crisis management.

Bespoke Announces Strategic Partnership with Leader Bank and Inclusion in Startup Innovation Toolkit Bespoke is thrilled to unveil a strategic partnership with Leader Bank, a renowned venture capital (VC) and private equity (PE) group based in Boston. This collaboration marks Bespoke's inclusion in Leader Bank's esteemed Startup Innovation Toolkit, a platform dedicated to supporting early-stage companies. Leader Bank has established itself as an outstanding advocate for early-stage businesses in the Boston area, providing crucial financial support and guidance. Through this strategic partnership, Bespoke aims to contribute its expertise in leadership and strategy consulting to Leader Bank's clients, further enhancing the growth and success of startups in the region. To learn more about Leader Bank's Startup Innovation Toolkit and the partnership with Bespoke, please visit the site below!