Every trade business owner eventually stares at a job that feels a size too big. A council tender, a national facilities contract, a body corporate that wants twelve sites serviced instead of one. Most talk themselves out of it before they price it, because the competitor looks bigger and the paperwork looks heavier. If you want to know how to win bigger contracts without the win sinking you, it helps to hear from someone who has taken that swing more than once.
Matt Jones sits down with Rafael Diaz, co-founder of Diaz Group LLC in Chicago. Rafael grew up on his father’s landscape crews, started the company with his brother in 2007, and has taken it from residential patios to commercial work, City of Chicago municipal contracts, a national subcontractor network and now its first contract in Mexico. His position is simple: winning the contract was never the risk. Delivering it is.
Below is the framework Rafael uses before every bid, how he sets up delivery once the contract lands, and why he says hiring never stops.
How to win bigger contracts: the four checks before you bid
Rafael runs the same four checks before bidding on any contract, and if one fails, he walks away no matter how much he wants the job.
First, pricing. In residential work the owner often sets the price. In commercial and government work you are up against businesses that have sat down and worked out their pricing model, so you need to know your own numbers and the market rate before you submit anything. Second, the contract itself. Corporate and municipal agreements carry clauses that can cost you money if you miss them. Rafael has someone with paralegal knowledge read every contract and sends anything flagged to an attorney on retainer. He admits contracts have slipped through the cracks in the past and cost the business money, which is exactly why the check exists. Matt has covered this ground before in an earlier episode on contract negotiation for trade business owners.
Third, capacity. Not just whether you have the trucks and crews today, but how quickly you could add four more teams if the bid lands. Fourth, and Rafael calls this the most important, whether your leadership team can take the pressure that comes with it.
Have the capacity conversations before you win
Rafael’s point on capacity is not that you need everything in place before you bid. It is that you need a plan. Before the tender goes in, he is already talking to the vehicle dealer and the equipment supplier: if I win this, can you lease or sell me four trucks, can you have ten mowers in my yard the next morning? Those conversations are easy to have and the answer is often yes. Waiting until the contract is signed to start asking is where smaller contractors get caught.
The same logic applies to people. Rafael’s business is always hiring, and recruitment runs through the same community involvement that drives his marketing: announcements through local churches and community centres, plus TV, radio, YouTube and online ads when a pipeline needs filling. In his words, if you are just waiting for people to turn up, you are not going to have them when you need them. An earlier Site Shed episode on what to consider when hiring contractors covers the other side of that decision.
Breaking a contract down and holding quality across crews
When Diaz Group wins a municipal contract in a new area, the work does not go to employees. It goes to subcontractors Rafael calls vendor partners. The first step is to break the contract down by scope and square metres, then work out how many pieces of equipment are needed and which partners have them, or whether the job is split between several. Rafael describes this as the moment the work becomes project management, and says how the handoff is done decides whether the contract succeeds.
Quality control then runs through internal field supervisors who do the rounds on every site, and account managers who own both the customer relationship and the subcontractor relationship for the life of the contract. Crucially, Rafael does not just hand a partner a job and hope. He vets their equipment before they start, leases or finances machines through his own rental company if theirs will not do the job, and offers training through Master the How, another business in his ecosystem. If you want subcontractors to follow your standard, he says, you have to give them the resources to do it.
Why leadership readiness decides the bid
Rafael’s fourth check is the one most owners skip. Going from managing ten people to twenty is a change, and supervisors who cannot pivot quickly under that pressure will break the contract regardless of how good the systems are. He hires for that attitude from day one, sets clear decision-making parameters so good people do not go off track, and promotes from within rather than poaching, because in his experience poached staff make bad employees.
Every new hire, from a field worker with a rake to a junior salesperson, goes through the same four-step onboarding: company history, company culture, how the engine works, and how their position affects everything else. Field crews get a boot camp of roughly four to five days plus weekly tailgate trainings, and office staff are reviewed every six months rather than yearly because, as Rafael puts it, waiting a year can be too late. It is a close cousin of the framework Vicky Irwin laid out in the Site Shed episode on fixing broken onboarding, and the culture piece echoes an earlier conversation on building a winning trade business culture.
The one thing Rafael will not do is over-analyse. Check pricing, contract, capacity and leadership. If all four hold, bid. If they do not, he says, your ambition is a notch too high for now, and that is fine. For a local look at the same problem, Matt’s earlier episode on how tradies can secure council contracts is a good companion listen.
Listen to the full episode above or watch it on YouTube to hear Rafael’s take on going international, the H2B visa idea behind his Mexico expansion, and why 60% of his revenue comes from snow. If the bigger contract is on your radar and you want the marketing and lead flow to match, book a free strategy call with the Tradie Web Guys team.
🫱🏻🫲🏼 Book a Free Strategy Call: https://tradie.wiki/tssyt
