Choosing a contractor for IT projects is one of those decisions that, if ill-considered, can cost a company a lot. The success of implementations, data security and effective use of the budget depend on it. In this category you will find practical guides about different models of cooperation with technology providers. We explain how to choose a company to build a website (such as WordPress or a store on WooCommerce), what to look for when choosing an ERP or CRM integrator, and how to assess the competence of a team developing web applications. We discuss billing - from fixed-price to time&material - and present fairly objectively the advantages and disadvantages of working with freelancers, small software houses and large companies: a larger organization does not always give better results, and a lower price may hide risks. We have prepared practical checklists for creating specifications, evaluating bids and testing skills (technical tasks, live coding, portfolio verification). We also highlight maintenance contracts, SLAs, SaaS vs. on-premise models, and hybrid solutions - with special emphasis on data security and regulatory compliance, as this often determines the choice of an external provider.