14 Recommendations for the First 30 Days of Fractional Leadership Engagement

Stepping into a fractional leadership role comes with unique challenges and opportunities, especially in the crucial first month. To provide you with seasoned insights, we've compiled fourteen top recommendations from Fractional CTOs, CEOs, and other key leaders. From the importance of listening before speaking to establishing relationships and clear goals, discover the essential best practices for the first 30 days of a fractional engagement.

Listen Before You Speak

In the first 30 days of a fractional engagement, my top recommendation is to listen more than you speak. Spend ample time understanding the client's culture, pain points, and goals—and the customer's, if possible—and resist the urge to impose immediate changes; instead, focus on building rapport and trust. 

This approach lays a solid foundation for collaboration and ensures that future recommendations and changes are informed by a deep understanding of the client's—and customer's—needs.

Sarah Eppler, Owner and Chief Marketer, Sarah Eppler Co.

Follow a Formal 30-Day Plan

Within the first 30 days of a fractional assignment, I have a formal 30-day project plan that I follow. The “essence” of that plan is twofold. First, LISTENING to ALL sides, from management to the lowest-level individual contributor.

Both sides “hear” each other, but RARELY LISTEN to each other. Seek first to understand, not to be understood. Secondly, a rock-solid, fact-based inventory of their technology: hardware, software, services, vendors, and the strategic/tactical plan to accomplish the business's goals.

Dale Bondanza, Principal Consultant, DAB Enterprises, LLC

Align Expectations and Assess the Organization

In the first 30 days of a fractional leadership engagement, it's crucial to establish a strong foundation and align expectations with the organization. Take the time to assess the organization's current state, its processes, and its challenges. This assessment should include: 

1. Engaging with key stakeholders, including executives, team members, and relevant staff. Understand their perspectives, expectations, and concerns. 
2. Reviewing existing workflows, systems, and procedures. Identify areas of improvement and efficiency gains. 
3. Assessing the company culture, values, and communication channels. Understand the dynamics among team members and any existing challenges. 
4. Examining financial statements, budgets, and forecasts. Identify any immediate financial concerns and opportunities for improvement. 
5. Analyzing the industry, market trends, and competitive landscape. Identify potential threats and opportunities. 
6. Communicating effectively in the initial days. Clearly articulate your role, responsibilities, and the specific goals you aim to achieve during your fractional engagement. Ensure that everyone understands the value you bring to the organization.
7. Establishing positive relationships with key stakeholders, both within and outside the organization. Develop a deep understanding of the team dynamics and foster an environment of trust and collaboration. 
8. Identifying and prioritizing quick wins that can be achieved within the first 30 days. This helps demonstrate your immediate impact and builds confidence in your ability to drive positive change. 
9. Working with key stakeholders to set clear, measurable goals and expectations for the fractional leadership engagement. This ensures alignment and provides a basis for evaluating success. 
10. Developing a strategic roadmap outlining the key initiatives and milestones for the duration of your engagement. This roadmap should align with the organization's broader goals and vision. 
11. Implementing regular feedback mechanisms to assess progress and address any concerns or adjustments needed. This could include regular check-ins, surveys, or open forums for team communication. 

By conducting a comprehensive assessment and following these best practices, you'll be better equipped to navigate the complexities of the organization and lay the groundwork for a successful fractional leadership engagement.

Krista Kupau, Co-Founder and CEO, Startup Talent

Set Clear Communication Lines

In the first 30 days of a fractional engagement, my top recommendation is to prioritize establishing strong, clear lines of communication with key stakeholders and deeply understanding the organization's culture, challenges, and objectives. This foundational period is crucial for building trust and rapport, which are essential for any leader, but especially so in a fractional capacity where time with the team is inherently limited.

Throughout these initial 30 days, maintaining flexibility and an open mind is crucial. Every organization has its unique challenges and opportunities, and a fractional leader must be adept at navigating these with a tailored approach. Regularly communicating progress, insights, and plans with the executive team and the broader organization helps in reinforcing the value of your role and ensuring alignment with the organization's vision and objectives.

Manoj Srivastava, Fractional CTO, Srivastava Consulting Group

Minimize Disruption, Understand the Client

Our firm is hired as a Fractional Sales Manager. We focus on getting in step with our client while causing minimal disruption during the first 30 days. Getting in step includes understanding the client's vision, values, and objectives. 

We'll then review the current department processes and written or unwritten expectations, which include job descriptions, sales processes, compensation, CRM, onboarding, and orientation. 

We'll then meet with our new team and department managers to clarify what we are learning and listen for communication or process challenges. We also begin conducting team meetings, but these are more for getting in step and building rapport than implementing quick change. 

When our clients see that we are highly interested in learning about them more than implementing disruptive change, it sets the stage for the next 30 days of tuning up and introducing improvement initiatives.

Rene Zamora, President and Founder, Sales Manager Now

Alleviate the Fear of Change

The first 30 days of engagement set the tone for your effectiveness as a fractional leader. The outsider perspective has a dual edge. One side brings unique value, and the other carries risk, mainly uncertainty.

For the organization to benefit from your unique perspective, the fractional leader must build trust and alleviate fear of change.

Before accepting the fractional engagement, align with the CEO about your plan for building affinity with key functions such as finance, business intelligence, marketing, sales, and customer success.

Leverage the outside perspective to ask curious questions about how things are done at the organization. Seek to understand what is working and where there are logjams.

Another fundamental approach to building trust is fixing problems. Find things that bring friction to people’s work or the quality of work-life experience. Establish yourself as a uniter of people whose purpose is to share in the creation of value to customers and the organization.

David LaCombe, Founder Fractional CMO, Imperatives Delivered

Build Trust with the CEO and Directors

Establishing trust with the CEO or Board of Directors is crucial for a successful engagement in any fractional relationship. To achieve this, you must actively listen to their directions and needs and seek clarity when necessary. 

It is also important to build productive relationships with other leaders by staying in your lane of responsibility and helping them when asked. Create an action plan and deliver on your promises within the given timeframe and to the expected standards. 

Additionally, follow up with the CEO and communicate transparently about the challenges you plan to overcome. Building trust, maintaining open communication, and delivering on your commitments demonstrates the long-term value you can bring to the company.

Paul Raggio, Owner, Five Star Leader Development

Engage in a Deep Immersion Phase

In the first phase of a fractional engagement, each party should set aside time for a 'deep immersion phase.' The organization should share their long- and short-term goals, current challenges and opportunities, and let the fractional leader become immersed in the day-to-day operations. 

On the fractional leadership side, they should focus on making sure they're asking the right questions to truly understand the organization's needs and begin developing a roadmap to achieve success aligned with those goals. 

With both parties focused on being open and engaged, this will provide the mutual understanding the team needs to set effective goals and priorities for a successful outcome.

Dan DeGolier, Founder and CEO, Ascent CFO Solutions

Gain 360-Degree Business Insight

Dig in right away! Our team of fractional accountants and CFOs starts an engagement by providing client companies with a detailed list of what we need access to and visibility on. This includes everything from the expected, such as bank and credit statements, loan and asset schedules, and existing forecasting documents, to their cap table, org chart, tech stack, and even marketing materials. 

We prioritize getting up to speed on not only the company's financial position but also their culture, operational workflows, stakeholder dynamics, and current and future products.

This 360-degree business view provides us insight into the biggest pain points for stakeholders to deploy our resources there first and provide value immediately. Often, this comes in the form of identifying cost savings, clarity in reporting, quick responsiveness, and full transparency.

Emily Arnold, CEO, Mesa Advisors

Prioritize Business Context and Relationships

As a fractional leader stepping into a new engagement, the first 30 days are crucial for setting the tone and creating momentum. This is your audition for the role! My top recommendations for this period are to prioritize your understanding of the business context and relationship-building. 

1. Customer Understanding: Start by focusing on the customer. Dive deep into understanding not only the Ideal Customer Profile (ICP) but also the existing customer base. Engage with customers through conversations, observations, and empathy exercises. This relational approach helps gain insights into their pain points, needs, and preferences, fostering a deeper understanding of the customer landscape.
2. Product or Service Offering: Forge relationships within the organization by immersing yourself in the product or service offering. Engage directly with the sales cycle, collaborate with product teams, and communicate with frontline staff. By building relationships across departments, you can gain a comprehensive understanding of the product's strengths, weaknesses, and roadmap, as well as the commercial model, pricing, and margins.
3. Cash Flow Analysis: Develop relationships with finance and operations teams to understand the organization's financial position. Analyze cash flow statements to gain insight into the organization's financial health, as this will inform your priorities for the next 30 days. Building rapport with key stakeholders in finance and operations allows for a collaborative approach to addressing financial concerns and optimizing cash flow management.

Fostering connections and trust with stakeholders is prioritized throughout this process of understanding the customer, product/service offering, and cash flow dynamics. Be sure to go about this in an iterative manner, adapting to the organization's existing cultural cadence for both communication methods and tone.

Marcie Jones, Growth, Fractional Leader

Immerse in Culture, Review Talent Processes

In the first 30 days of any fractional assignment, I find it best to immerse yourself in the culture and work environment to gain an understanding of your client's best attributes and biggest potential risks. 

A thorough review of the talent acquisition, candidate experience, talent management, and talent development processes and programs will provide a solid foundation. 

Change for the sake of change is never a good use of resources. By creating awareness and gaining authentic insights, positive change will follow. The goal is to create or enhance their retention-focused culture.

Mark Krajnik, LSSGB, CPC, Fractional Chief People Officer, Performance Mindset Associates

Grasp Company's Current State

In the first 30 days, getting a solid grasp of the company's current state is key. We follow a checklist (that we developed) with our clients that covers several critical areas: reviewing the company's strategy, objectives, budget, cash-flow projections, and key performance indicators (KPIs). 

This approach ensures we have a comprehensive understanding of where the company stands. Based on this insight, we then prioritize and outline a 90-day plan focused on addressing the most pressing priorities and objectives.

Jaime Trujillo-Ramirez, Fractional CFO, MLHC

Assess, Align, and Act with AI

“Assess, align, and act” encapsulates my strategy in the crucial first month of a fractional CMO role. It's about delving into the company's marketing ecosystem, ensuring strategies resonate with the overarching business goals, and then taking decisive steps toward a future marked by robust growth and relentless innovation. 

This approach lays a solid foundation for marketing success. In today's fast-paced digital landscape, leveraging the right automated tools and AI technologies is not just an option; it's a necessity. As both a fractional CMO and a coach to emerging leaders in this space, I emphasize the importance of adopting cutting-edge AI solutions that can analyze data in real-time, predict consumer behavior, and personalize marketing efforts at scale. 

This intelligent integration not only streamlines operations but also significantly enhances the effectiveness of marketing campaigns, ensuring that we're not just keeping pace but setting the pace in a competitive market.

Kirsten Zaremba, Fractional CMO, Loop Now

Establish Relationships and Clear Goals

One should prioritize building relationships with key stakeholders and team members to understand the organizational culture and expectations. Set clear, achievable goals and metrics that align with the organization's long-term vision to guide your efforts effectively. 

Establish transparent communication channels for regular feedback, ensuring all parties are aligned and informed. This foundation of trust, clarity, and strategic focus is essential for a successful fractional engagement.

Stephen Martin, Fractional CTO, Martin Tech Labs

This list is packed with incredible insights! We hope that you've found inspiration from these remarkable experts. Gleaning wisdom from their experiences can propel our leadership growth. We're immensely thankful for our community of fractional leaders. If you're a fractional leader looking to join our pool of fractional experts, we'd be thrilled to hear from you. Contact us today—we can't wait to meet you!