
Historian Doris Kearns Goodwin popularized the term "Team of Rivals" in her 2005 book of the same name1. It refers to President Abraham Lincoln's strategy of appointing a diverse group of individuals to his cabinet, the most prominent of whom were his rivals during the 1860 presidential election. Despite their initial animosities towards Lincoln and each other, these individuals accepted Lincoln's invitation to serve in his cabinet.
The brilliance of this strategy lies in its multifaceted nature. First, by bringing his rivals into his cabinet, Lincoln neutralized potential sources of opposition. Second, he was able to benefit from a wide range of perspectives and approaches to policy, which was particularly valuable in dealing with the unprecedented challenges of the Civil War.
Lincoln demonstrated exceptional emotional intelligence and political acumen in managing this team. He was patient, inclusive, and willing to listen to differing viewpoints. He wasn't afraid of disagreement and welcomed debate in his cabinet meetings. This approach allowed him to leverage the collective intelligence of his team to make more balanced and informed decisions.
In essence, the "Team of Rivals" concept is a testament to Lincoln's leadership philosophy, which prioritized the good of the nation over personal ambition or rivalry. His ability to manage and harness the strengths of this diverse team played a crucial role in guiding the United States through the Civil War.
Sadly, implementing a "Team of Rivals" approach, like Abraham Lincoln did, is extremely rare, and can be quite challenging for reasons mostly having to do with being human:
These factors make the "Team of Rivals" approach a complex and risky leadership strategy. It requires a strong leader with exceptional interpersonal skills, conflict management abilities, and a willingness to take on the considerable challenges of this kind of team. These requirements may explain why this approach is not widely adopted, despite the compelling example set by Lincoln. Few of us have been given or developed all of these necessary skills.
But what if you could get a lot of the benefits of such a team without the drama, conflict, and energy-sapping ego management? What if you could get these perspectives without worrying about motives, hidden agendas, or even the rivalries themselves?
Using current Large Language Models like ChatGPT to challenge your own ideas has the potential to deliver at least some of the benefits of having rivals criticize your work, while mitigating issues related to ego and competition in decision-making processes.
Now that we have powerful AI tools at our disposal, perhaps we can use them to form our own, personal “Team of Rivals” -- without the annoying baggage that dealing with pesky humans can bring.
Crafting a prompt to invite challenge from ChatGPT involves clearly stating your idea and then directly asking the AI to critique, question, or provide alternative viewpoints. Here are some examples of simple prompts you could use to demonstrate the idea:
So how can we try this out? Well, any planned endeavor could do – a marketing campaign, new product idea, business expansion plan, etc. Let’s try a simple business idea for our example:
Here’s my proposal: Cyclists love coffee (and beer, too, but let us focus on the coffee for now). Coffee, and especially espresso, is intertwined with the long history of cycling, both at the beginning and end of rides.
I love coffee with my cycling, but too many times rides start or end far from a good café. So, I have had the idea for some time now for a mobile espresso service that caters to cyclists. But is it realistic? Can it be a real business? Could it be franchised and be the next Starbucks?
Our Bicycle-powered Espresso cart as imagined by BlueWillow AI
We’ll go now to ChatGPT and set up our scenario, much as we did in the last article, and as I’m sure you recall, our setup template is:
This example session will focus on ways we can use an AI to refine and challenge our assumptions. I’m going to include the complete dialog I had with ChatGPT (version 4, to be specific) so you can see the flow and the change from mentoring to the refining of ideas, and finally creating some an alternative viewpoint, as well as some devil’s advocacy:
Human
Your role: Please take the role of an entrepreneurial advisor - an expert in new business startups who has started many small businesses. Reply only with "OK" if you understand your role.
ChatGPT
OK
COMMENT: As mentioned in prior articles, we use “Reply only with ‘OK’” in the prompt so that ChatGPT doesn’t jump in with a lot of irrelevant banter prior to understanding the task. These “junk” responses will become part of the context of our discussion – and we don’t want that until we’re ready, so we explicitly ask the AI to hold its fire, for now.
Human
My role: I am considering starting a small business with a unique idea and I am coming to you for help and advice on my idea. Reply only with "OK" if you understand my role.
ChatGPT
OK
Human
Context: Here's my business plan: It is well known that bicyclists love coffee, both before a ride and after. However, many places that rides start and end, such as city parks, have no coffee available nearby. With a portable espresso bar, I could service that need by moving the cafe to the cyclists where they start and end their rides. The espresso bar would be moved by pedaling an attached bike, thus tying the bar even more to the culture of cycling. If you understand this context, please respond only with "OK".
ChatGPT
OK
Human
The Task: I want you to evaluate my proposed business idea. First, ask me any questions you have that will assist in your analysis. Please focus on profitability.
ChatGPT
Absolutely, I'm happy to help you evaluate this. Here are some key questions:
Human
Those are great questions. Here are my answers:
COMMENT: Note that we can answer all of the posed questions in one response, and we can make it easier for ChatGPT to match the response to the question by using the same numbers as the AI did in their questions.
ChatGPT
Thank you for the additional information. Here is a basic profitability analysis based on the information you've provided.
Revenue: If we consider an average of 20 cyclists per day, let's assume that half of them (10) buy a coffee drink. This could vary, but it's a conservative starting point.
Adding in the sale of snacks or ride food can significantly increase your profit margin. Let's say you sell snacks to 5 people per day, with an average cost of $3 per snack. That's an additional $15 per day.
So your total daily revenue is estimated at $58.
Costs: The primary upfront cost is the Velopresso pedal-powered coffee trike for $15,000. Then there are the ongoing costs of coffee, milk, snacks, cups, and other supplies. Assume for now that this averages $15 per day, based on your estimated customer numbers.
The number of working days per year will affect your profitability. If you work 6 days per week for 52 weeks, that's 312 days per year.
Profitability: Daily revenue ($58) - daily costs ($15) = $43 profit per day Annual profit = daily profit ($43) * 312 days = $13,416
Keep in mind this doesn't include taxes and any unforeseen costs.
Given this, it would take a little over a year to recover the initial investment of $15,000 (approximately 1.1 years). After that, you should be profitable, based on these estimates.
The potential for profitability seems reasonable, but it relies on maintaining consistent customer numbers and managing costs effectively. And, of course, it's based on a series of estimates, so the actual figures could be somewhat different.
Does this basic analysis help give you an idea of the potential profitability of your business?

Cyclist with espresso. photorealistic mage generated by BlueWillow AI
Human
That helps. I think we should consider tips. As this is in the US with a "tipping culture" I think we could assume 15% tips on average in addition to the regular income. Since this would be a solo venture with no employees, we can add those tips to the revenue.
ChatGPT
That's a good point. Tips can indeed contribute a significant amount to your total earnings, particularly in the U.S. where tipping is customary.
Given your pricing, the average cost per drink comes out to about $4.00, and with 10 drinks sold per day, that's $40.00 in sales per day from drinks. At a 15% tipping rate, you could expect about $6.00 per day in tips from drinks.
For snacks, using the same logic with the average cost of $3.00 per snack and selling 5 snacks per day, that's $15.00 in snack sales per day. At a 15% tipping rate, that's about $2.25 in tips from snacks.
So, tips could potentially add an extra $8.25 per day, which over 312 operating days would equate to an additional $2,574 annually.
This would bring your total annual profit to $15,990 ($13,416 + $2,574), reducing the time it takes to recover your initial investment to just under a year. This does make the business look more attractive from a financial perspective.
As always, this is a rough estimate, and actual figures could be somewhat different. For instance, in good weather or during special events, you might see an increase in customers and therefore in tips. Conversely, there may be quiet periods where tips are lower. It's also worth noting that the quality of service and the quality of your product can significantly impact the amount of tips you receive.
Human
For the next part of the conversation, I'd like you to take a look at this idea from the viewpoint of a customer... what would they think? How could the experience be improved for them?
ChatGPT
Absolutely, looking at the idea from the perspective of a customer is crucial. Here are a few aspects to consider:
Remember, the goal is to create an experience that is so positive and unique that your customers want to return and tell their friends about it. That's the best kind of marketing you can have!
Human
Thank you. The idea on sustainability seems very important. Do sustainable supplies like cups cost a lot more?
ChatGPT
Sustainable or eco-friendly supplies like cups, lids, and straws generally do cost more than their traditional, non-recyclable counterparts. The price can vary significantly depending on the specific materials used, the supplier, and the quantity you buy, among other factors.
For instance, traditional plastic cups can cost a few cents each when bought in bulk, while compostable or biodegradable cups might cost two or three times as much. However, prices have been decreasing over the years as more businesses switch to eco-friendly alternatives and as production processes become more efficient.
While these supplies may increase your costs, many customers are willing to pay a bit more for a product when they know the business is committed to sustainability. You could consider explaining the extra cost to your customers and even adding a small surcharge to cover it, if necessary. Alternatively, you could absorb the extra cost as a part of doing business in a way that aligns with your values and those of your customers.
Lastly, you might be able to mitigate some of the additional costs by taking advantage of bulk buying or negotiating deals with suppliers. You could also explore opportunities for grants or incentives aimed at promoting sustainable practices in small businesses.
Keep in mind that while sustainability may come with added costs, it also opens up opportunities for marketing and customer engagement. Many consumers are actively seeking out businesses that align with their values, including environmental responsibility.
Human
Cool. One thought - this would generate a large volume of used coffee grounds - how can they be recycled?
ChatGPT
Great point! Coffee grounds are rich in nutrients and can be put to several good uses, reducing waste and potentially providing additional benefits. Here are a few possibilities:
One caution, however: coffee grounds are acidic, so they should be used judiciously in gardens and compost to avoid creating overly acidic conditions.
Remember, promoting your use of coffee grounds in these ways can also contribute to your business's image as environmentally responsible. It's another point of interest for customers who value sustainability.

The Velopresso bike-powered coffee cart from https://www.velopresso.cc/
Human
For the next section, please play the role of devil's advocate and tell me why this espresso cart idea won't work!
ChatGPT
Absolutely, playing devil's advocate can be a useful exercise in identifying potential challenges. Here are a few things to consider:
Remember, recognizing potential challenges is the first step towards mitigating them. Even with these issues in mind, you can still make a success of your business with good planning and adaptability.
Human
Please switch your role back to being an entrepreneurial mentor. Given all of the above, what is your best advice on whether or not to move forward on this idea.
ChatGPT
As your entrepreneurial mentor, my advice is based on a combination of your business plan, financial analysis, customer experience, sustainability concerns, and potential challenges.
From the analysis we've done, your business idea has several strong points:
However, there are also challenges to consider:
In light of these factors, here are my recommendations:
Remember, every business comes with risks, and not all will be successful. However, careful planning, a clear vision, and a willingness to adapt can go a long way toward ensuring your business thrives. Good luck!
(End of ChatGPT Transcript)
Indeed!
Of course, while AI tools can provide you with a potentially useful tool for challenging your plans and ideas while reducing ego or competition-related problems, it is not a complete substitute for human interaction and leadership. It can be an aid in the process, providing a new perspective and additional insights, but it will, of course, miss many of the nuances of human dynamics that are often troublesome, but also can lead to surprising breakthroughs when managed well.

Happy Trails - Image by BlueWillow AI
References:
1 Team of Rivals: The Political Genius of Abraham Lincoln, Doris Kearns Goodwin, Simon & Schuster, 2005