From Solo to Synergy: Harnessing OKRs to Transform Your Team into Co-Founders — Part 1

Photo by Emilio Garcia on Unsplash

How can you brief your team to successfully create OKRs? This article is the first in a five-part series to answer this question based on my hands-on experience as a startup founder.

From 2019 to 2023, I built a SaaS startup in the retail space. Despite choosing one of the most challenging business models — a two-sided platform — and closing down the business due to the economic downturn & pandemic, my team and I managed to win several awards and acquire international OEMs as our customers.

As a solo founder, everyone advised me that I needed a co-founder — and they were right. However, since I couldn’t find the right fit, I had to seek an alternative solution. This challenge turned out to be one of the most instructive experiences of my life. I learned to empower my team of junior full-time employees (FTEs), working students, and interns, helping them to expand their expertise beyond their initial roles. This enabled them to evaluate the impact of their actions in relation to the company’s goals.

In essence, my team became my co-founder.

We implemented a specific workflow that allowed us to build, operate, and refine our business model with both speed and quality, utilizing a combination of OKRs (Objectives and Key Results) and Scrum.

This article is crafted as a manual for pre-Series A startups aiming to work on quarterly goals and strategy. It provides a step-by-step guide on how to engage team members in the strategic planning process, fostering a sense of ownership and alignment with the company’s vision. By integrating insights from SWOT and TOWS analyses into the OKR Briefing, each team member gains a comprehensive understanding of the company’s internal and external environment, enabling them to craft their own objectives and key results more effectively.

Understanding SWOT and TOWS

SWOT Analysis is a strategic planning tool that enables organizations to evaluate their current position and potential growth prospects by identifying their:

• Internal-Strengths
• Internal-Weaknesses
• External-Opportunities
• External-Threats

TOWS Matrix is used to generate strategies by leveraging the insights of the SWOT-Analysis. TOWS matrix focuses on four key strategies:

• Strength — Opportunity: How can strengths be maximized to seize opportunities?
• Strength — Threat: How can strengths be maximized to mitigate threats?
• Weakness — Opportunity: How can opportunities be utilized to offset weaknesses?
• Weakness — Threat: How can weaknesses be minimized to mitigate threats?

Creating a SWOT-Analysis with your team leads (90 Min.)

SWOT analysis example

Invite team members who work at the intersection between strategy and execution (e.g. team leads) for a well-rounded perspective. Once you have everyone in place, start an open discussion using the SWOT-Analysis template and document your team’s statements.

Keep in mind: Even though the questions covered in this article seem very detailed and time-consuming, you should aim to collect the statements for each part of the SWOT-Analysis in ideally 90 minutes. Not every question shared in this article needs to be answered, especially for early-stage startups who lack the data or experience to do so. Also based on my personal experience exceeding this time limit not only lowers your team’s motivation, but also leads to a more hypothetical than fact-based discussion. So, keep it focussed and have fun ✌🏼

How to Identify Internal Strengths?

Focus on your advantages in product innovation, sales performance, marketing reach, available resources, team capabilities or financial robustness. Use the following questions for a more detailed analysis of your strengths if needed:

• Unique Resources: What resources do you have that are unique or hard for competitors to duplicate or acquire? This could include features, patents, proprietary technology, strong brand, strategic locations, or highly skilled personnel.
• Operational Efficiency: Is your company particularly efficient at producing its goods or services? Do you have a strong supply chain or cost-effective production methods?
• Strong Financial Position: Do you have good profitability, a solid cash flow, or high liquidity that gives you a financial advantage over competitors?
• Customer Loyalty: Do you have a strong customer base that is loyal to your products or services?
• Market Leadership: Are you a leader in your market segment? This might be in terms of market share, brand recognition, or reputation for quality.
• Strong R&D Capabilities: Do you have a history of innovation? A strong research and development department can be a significant strength.
• Positive Organizational Culture: Do you have a positive workplace culture that attracts and retains top talent?

How to Identify Internal Weaknesses?

Highlight areas for improvement such as product offerings, sales processes, marketing strategies, resource availability, team skills or financial standing. For a deep dive to identify your weaknesses try the following questions:

• Resource Limitations: Do you lack any key resources that could prevent you from taking advantage of opportunities or responding to threats?
• Operational Inefficiencies: Are there parts of your operations where you’re less efficient than competitors, such as longer production times or higher costs?
• Weak Financial Position: Do you have high levels of debt, low profitability, or cash flow issues?
• Customer Retention Issues: Are you struggling with low customer loyalty or high churn rates?
• Poor Market Position: Are you lacking visibility in the market or struggling to compete with established brands?
• Limited R&D Capabilities: Do you lack the capability to innovate and stay ahead of market trends?
• Negative Organizational Culture: Is your workplace culture toxic or uninviting, leading to high staff turnover or low morale?

How to assess external Opportunities?

Assessing external opportunities requires you and your team to explore customer segments, emergent market trends or competitors’ weaknesses that could be capitalized on. The following questions may help for a deep-dive discussion if needed:

• Market Trends: Are there any emerging market trends that we can capitalize on? How is customer behavior changing and how can our business respond to these changes?
• Competitor Vulnerabilities: What are the areas in which our competitors are underperforming? Can we exploit these weaknesses to gain a competitive advantage?
• Economic Factors: How can changes in the economy or our industry create opportunities for us? Is there an economic trend that benefits the growth of our sector or business?
• Technological Innovation: What new technologies are available that can enhance our product/service or operations? How can we use technological advancements to our advantage?
• Changes in Government Policy or Regulations: Are there any new or upcoming regulations that might create business opportunities for us? Are there changes in governmental policies that we could leverage for business growth?
• Changes in Social Patterns, Population Profiles, Lifestyle Changes etc: Are there demographic changes or shifts in societal behavior that can create new opportunities for us? What are the emerging lifestyle trends that align with our products or services?
• Global Events: How can we leverage global events or shifts in the macro environment to our benefit? Have recent events created a new need that we can address?
• New Markets: Are there unexplored markets (geographical or demographic) where our products or services may have a demand? Is there an opportunity for expansion or diversification?

How to identify External Threats?

Identify hurdles like shifting customer behavior, evolving market trends or competitors’ moves that could pose risks to your business. As usual, the following questions can you help you to dig a little deeper:

• Competitor Actions: What strategies are your competitors employing? Are they launching new products or entering your market segments?
• Regulatory Changes: Are there any upcoming government regulations that could negatively impact your business?
• Economic Downturn: Are there signs of an economic downturn that could reduce demand for your product or service?
• Technological Changes: Are there new technologies that could make your product, service, or operations obsolete?
• Market Saturation: Is your target market becoming saturated, making it harder for you to maintain or grow your market share?
• Changes in Consumer Behavior: Are consumers’ tastes changing in a way that could decrease demand for your product or service?
• Supply Chain Risks: Are there potential disruptions in your supply chain due to political instability, environmental factors, or other risks?
• Societal and Environmental Changes: Are there societal shifts or environmental concerns that could pose a threat to your business? For instance, increasing awareness about climate change might pose a threat to businesses with a high carbon footprint.
• Financial Risks: Are there financial risks such as rising costs, decrease in funding or investment, or currency fluctuations that could affect your business?

Merge and prioritize the Statements

Once there are no more statements to add, start merging similar ones for a clearer view in the SWOT-Analysis template. Once this is done, prioritize the statements in each box based on their significance and impact on the organization.

💡 Note: The SWOT analysis will be more effective if based on factual data rather than personal opinions.

How to generate strategies with theTOWS Matrix

TOWS matrix example

Now you have the information needed to assess the status quo of your company and later on, share it with your complete team. Working on TOWS will enable you and your team leads to assess the strategies needed for the upcoming OKRs and act as a valuable counterpart in the discussions to come. Let’s go!

Transfer your SWOT analysis findings to the TOWS Matrix template and divide the team that helped you to create the SWOT-Analysis into groups and assign each one a specific pairing:

• Strengths-Opportunities (SO)
• Weaknesses-Opportunities (WO)
• Strengths-Threats (ST)
• or Weaknesses-Threats (WT).

Ask each group to come up with a maximum of three strategies for the next quarter based on their pairing:

• Strength — Opportunity: How can we use our strengths to capitalize on opportunities?
• Strength — Threat: How can we leverage our strengths to counter threats?
• Weakness — Opportunity: How can we take advantage of opportunities to address our weaknesses?
• Weakness — Threat: How can we reduce our weaknesses to avoid threats?

Once every team is done, have a brief discussion and if needed refine these strategies.

💡 Note: This isn’t about perfect strategy. It’s pre-work for the OKR briefing to help everyone — even non-participants — identify their own strategies to effectively phrase OKRs.

After analyzing the company’s situation through SWOT and deriving strategic suggestions via TOWS, it’s time to create an OKR briefing for your team. This briefing should include the necessary to enable them to derive their OKRs.

Understanding the OKR-Briefing

• The first step towards defining quarterly objectives & key results is the OKR briefing executed by the CEO and/or Team Leads.
• During this meeting, the CEO or Team Lead updates the team on the company’s current status, customers, business model, market trends, and strategic themes for the next quarter.
• This briefing aims to provide everyone with a comprehensive understanding of information beyond their daily work, department, and expertise, ensuring an equal level of knowledge among the team.
• The briefing should enable team members to create OKRs, considering their expertise, available resources (time, money, personnel), customer needs, and market trends.
  Click here to access my OKR-Briefing Template

How to create the OKR-Briefing

1. Product Update

Establish a review of product KPIs tied to growth, retention, and uptime, incorporating key insights from their evolution, to help team members learn from previous successes or failures.

Next up, provide an overview of new features or modifications to existing ones that were rolled out prior to the OKR, highlighting their value proposition. This allows the team to have a broad understanding of the progress made and the current state of the product.

Make sure to also highlight the contribution of these features to internal growth and retention-related KPIs, as well as KPIs related to customer success (CSM). Relating product development to business KPIs helps the team understand the feasibility between development, sales/marketing, and finance in business modeling.

If applicable, also provide updates on pricing changes, ensuring to clarify their reasons (e.g., customer feedback, faster market adoption, etc.).

2. Sales Update

Start by developing a summary of existing customers, their contribution to company revenue, insights from customer feedback and demands, along with the next steps in the partnership. This is crucial for team members like UX designers, developers, and back-office staff who don’t directly interact with customers. It helps them understand what customers value in the product or service, identify what needs are being met or not yet met, and prioritize OKRs and feature development based on current earnings and potential growth. It also shows them the tangible value of their work.

Once you have covered the existing customers, make sure to provide an outlook on potential new customers.

Provide a breakdown of your sales pipeline, categorized by stages from initial contact to closing. Include opportunity size per prospect and in total per stage.

💡 Note: During the presentation focus on explaining acquisition methods (e.g., inbound, outbound), why prospects are interested, any product gaps that might hinder deal closure, and any key features that sealed the deal.

3. Cashflow Forecast

Create a revenue forecast including a worst-case, middle-case, and best-case scenario for the next 6–12 months. To illustrate the revenue forecast, add information about new customers or upselling of existing customers to the middle case graph in the upcoming months.

Include a graph showing the company’s liquidity forecast or burn rate in relation to revenue.

💡 Note: Showcasing liquidity is crucial for pre-break-even startups as it helps team members understand when and how to achieve profitability, and raises awareness of the company’s runway, potential cost cuts, and the need for additional funding rounds.

4. Budget Allocation & Team building

Create an overview regarding expenses separated into marketing budget, personnel costs, and others for the upcoming 12 months. Make sure to include key marketing expenses to help your team derive technical and non-technical requirements or impacts for the upcoming OKR.

To enable departments to plan for onboarding or anticipate uplifts in productivity for the upcoming OKR, include information about new team members and their start date.

5. Market Trends & Strategic Scope Suggestions

This part of the briefing is crucial as it aids team members who don’t usually work with dashboards, offering them tangible ideas to formulate meaningful OKRs and boost their skills and confidence.

Share a simplified version of your TOWS matrix created earlier, highlighting strategy suggestions to handle outside influences like market trends and customer needs, and inside factors such as strengths and weaknesses.

💡Note: This matrix simplifies the process for your team to structure the company’s internal and external status quo for OKR development

Next up, share your key objectives and strategies for the upcoming quarter with a brief explanation of their purpose and expected outcomes. Suggest your epics for execution and metrics for success measurement.

💡 Note: Offer your views on strategy, epics, and metrics as suggestions, but not as a fixed roadmap. This encourages your team to ideate, formulate their own OKRs.

Executing the OKR-Briefing (90 Min.)

1. Guide your team through the 5 topics of the briefing and make sure you add the information missing to fully transport the message per slide by narrating.
2. This presentation is not a lecture but a mere discussion. Your team members should feel encouraged to question the purpose and sense of the information provided during the presentation
3. Remember the goal of the briefing is to have everyone on the team on the same level of knowledge. therefore make sure you share your briefing in an e.g. team chat/drive and add a Q&A at the end of the presentation

Once you’ve had the briefing, it’s time for your team members to roll up their sleeves and start preparing their own OKRs as explained in part 2 here✌🏼

If this was helpful, definitely check out my newsletter ‘TheGoodFlow.ai’ here to receive weekly snippets from my playbook, plus tips on using GPT to build, run, and scale your startup or reach out to me on Linkedin.